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 → 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

HRID 523194Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:26])[C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@H:9]([CH3:17])[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C@H:4]([C:27](=[O:44])[NH:28][C@:29]2([C:34](=[O:43])[NH:35][S:36]([C:39]3([CH3:42])[CH2:41][CH2:40]3)(=[O:38])=[O:37])[CH2:31][C@H:30]2[CH:32]=[CH2:33])[CH2:3]1.[C:45](OC(N[C@@H]([C@H](CC)CC(C)CCC=C)C(N1C[C@H](O)C[C@H]1C(O)=O)=O)=O)(C)(C)C.C(OC(NC([C@H](C)CC(C)CCC=C)C(N1C[C@H](O)C[C@H]1C(O)=O)=O)=O)(C)(C)C>>[CH2:17]([C@H:9]([CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([N:5]1[CH2:6][C@H:2]([OH:1])[CH2:3][C@H:4]1[C:27](=[O:44])[NH:28][C@:29]1([C:34](=[O:43])[NH:35][S:36]([C:39]2([CH3:42])[CH2:40][CH2:41]2)(=[O:38])=[O:37])[CH2:31][C@H:30]1[CH:32]=[CH2:33])=[O:26])[CH3:45]

Participants

Reactant 3

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 86683245(2S,4R)-1-((3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid

HCID 86683262(2S,4R)-1-((2S,3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

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

Procedure

The same procedure was used as described for the preparation 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 but (2S,4R)-1-((2S,3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid was used as starting material instead of (2S,4R)-1-((3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid. 1H NMR (400 MHz, DMSO-d6): δ ppm 10.42 (d, J=4.02 Hz, 1H) 8.83 (d, J=8.53 Hz, 1H) 6.24 (m, 1H) 5.81 (m, 1H) 5.57 (m, 1H) 5.05 (m, 5H) 4.32 (m, 3H) 3.59 (m, 2H) 1.92 (m, 8H) 1.25 (m, 21H) 0.84 (m, 8H) MS: MS m/z 653.4 (M++1)

Sources & evidence

ORD record: ord-15d535d6f4e4435c85fed016df0d65f2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334279B2

Reaction notes

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