tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-2-hydroxy-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate → tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-7-ethyl-2-hydroxy-9-methyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

HRID 523195Notes

Reaction equation

O[C@H]1CN2C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H](C)C[C@H](C)CCC=C[C@@H]3C[C@@]3(C(=O)NS(C3(C)CC3)(=O)=O)NC(=O)[C@@H]2C1.[CH2:43]([C@H:45]([CH2:81][CH:82]([CH3:87])[CH2:83][CH2:84][CH:85]=C)[C@H:46]([NH:73][C:74](=[O:80])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])[C:47]([N:49]1[CH2:53][C@H:52]([OH:54])[CH2:51][C@H:50]1[C:55](=[O:72])[NH:56][C@:57]1([C:62](=[O:71])[NH:63][S:64]([C:67]2([CH3:70])[CH2:69][CH2:68]2)(=[O:66])=[O:65])[CH2:59][C@H:58]1[CH:60]=C)=[O:48])[CH3:44].O[C@H]1CN(C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H](C)CC(C)CCC=C)[C@H](C(=O)N[C@]2(C(=O)NS(C3(C)CC3)(=O)=O)C[C@H]2C=C)C1>>[CH2:43]([C@H:45]1[C@H:46]([NH:73][C:74](=[O:80])[O:75][C:76]([CH3:77])([CH3:78])[CH3:79])[C:47](=[O:48])[N:49]2[CH2:53][C@H:52]([OH:54])[CH2:51][C@H:50]2[C:55](=[O:72])[NH:56][C@:57]2([C:62](=[O:71])[NH:63][S:64]([C:67]3([CH3:70])[CH2:68][CH2:69]3)(=[O:66])=[O:65])[CH2:59][C@H:58]2[CH:60]=[CH:85][CH2:84][CH2:83][C@@H:82]([CH3:87])[CH2:81]1)[CH3:44]

Participants

Reactant 3

HCID 75203843tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-2-hydroxy-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

HCID 86683198tert-butyl ((2S,3R)-1-((2S,4R)-4-hydroxy-2-(((1R,2S)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate

HCID 90128180tert-butyl ((2S,3R)-3-ethyl-1-((2S,4R)-4-hydroxy-2-(((1R,2S)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-5-methyl-1-oxonon-8-en-2-yl)carbamate

Product 1

HCID 75203842tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-7-ethyl-2-hydroxy-9-methyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

Procedure

The same procedure was used as described for of tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-2-hydroxy-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate but tert-butyl ((2S,3R)-3-ethyl-1-((2S,4R)-4-hydroxy-2-(((1R,2S)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-5-methyl-1-oxonon-8-en-2-yl)carbamate was used as a starting material instead of tert-butyl ((2S,3R)-1-((2S,4R)-4-hydroxy-2-(((1R,2S)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.32 (s, 1H) 7.01 (d, J=9.54 Hz, 1H) 5.38 (m, 2H) 5.08 (m, 1H) 4.40 (br. s., 1H) 4.20 (t, J=7.78 Hz, 1H) 4.00 (m, 1H) 3.67 (m, 2H) 2.85 (q, J=7.53 Hz, 3H) 2.22 (d, J=8.03 Hz, 1H) 1.84 (m, 4H) 1.29 (m, 22H) 0.84 (m, 6H) 0.48 (m, 2H). MS: MS m/z 625.4 (M++1).

Sources & evidence

ORD record: ord-9aa02f23d53e497cabe6ac4225934779
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334279B2

Reaction notes

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