HCID 54673085, compound → HCID 90060259, compound

HRID 1779211Notes

Reaction equation

HRID 1779211 reaction equation
OC(C)(C)[C@@H]([NH:5]C(C1C2C(=NC=C(C3CCCCC3)N=2)NC=1)=O)C.[C:25]([O:28][CH2:29][CH2:30][C@:31]([OH:73])([C@@H:35]([C:53](=[O:72])[NH:54][C@H:55]([C:68]([O:70][CH3:71])=[O:69])[CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][C:65]#[C:66][CH3:67])=[CH:59][CH:58]=1)/[CH:36]=[CH:37]/[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](=[O:52])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:32](O)=[O:33])(=[O:27])[CH3:26].[CH2:74]([O:78][C:79]1[CH:84]=[CH:83][C:82]([CH2:85][C@H:86]([NH:91][C:92]([C@H:94]([C@@:112]([OH:124])([CH2:120][C:121]([O-])=[O:122])[C:113]([O:115]C(C)(C)C)=[O:114])/[CH:95]=[CH:96]/[CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][C:103](=[O:111])[CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH3:110])=[O:93])[C:87](OC)=[O:88])=[CH:81][CH:80]=1)[C:75]#[C:76][CH3:77]>>[C:25]([O:28][CH2:29][CH2:30][C@:31]([C@H:35](/[CH:36]=[CH:37]/[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](=[O:52])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:53]([NH:54][C@@H:55]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][C:65]#[C:66][CH3:67])=[CH:59][CH:58]=1)[C:68]([O:70][CH3:71])=[O:69])=[O:72])([C:32](=[O:33])[NH2:5])[OH:73])(=[O:27])[CH3:26].[CH2:74]([O:78][C:79]1[CH:80]=[CH:81][C:82]([CH2:85][C@H:86]([NH:91][C:92]([C@@H:94](/[CH:95]=[CH:96]/[CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][C:103](=[O:111])[CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH3:110])[C@@:112]([OH:124])([CH2:120][CH2:121][OH:122])[C:113]([OH:115])=[O:114])=[O:93])[CH2:87][OH:88])=[CH:83][CH:84]=1)[C:75]#[C:76][CH3:77]

Participants

5

Reactant 3

HCID 54673085HCID 54673085, compoundHCID 90060133HCID 90060133, compoundHCID 131734862HCID 131734862, compound

Product 2

HCID 90060259HCID 90060259, compoundHCID 118157636HCID 118157636, compound

Procedure

No. 6801995, methyl (S)-2-[(E)-(S)-2-((S)-3-acetoxy-1-carbamoyl-1-hydroxy-propyl)-11-oxo-octadec-3-enoylamino]-3-(4-but-2-ynyloxy-phenyl)-propionate (ESI (LC/MS positive mode) m/z 685 (M+H); Rt 3.40 min.) was synthesized by the synthesis similar to that of No. 5453635, 2-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-hydroxy-1,2-dimethyl-propyl)-amide, except that No. 5214354, (E)-(2S,3S)-2-(2-acetoxy-ethyl)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-12-oxo-nonadec-4-enoic acid was used instead of No. 5317776, 1-tert-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate. From methyl (S)-2-[(E)-(S)-2-((S)-3-acetoxy-1-carbamoyl-1-hydroxy-propyl)-11-oxo-octadec-3-enoylamino]-3-(4-but-2-ynyloxy-phenyl)-propionate, the title compound was obtained by the synthesis by a synthetic method similar to that of No. 5257016, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-hydroxymethyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoic acid.

Workup

  1. custom6801995, methyl (S)-2-[(E)-(S)-2-((S)-3-acetoxy-1-carbamoyl-1-hydroxy-propyl)-11-oxo-octadec-3-enoylamino]-3-(4-but-2-ynyloxy-phenyl)-propionate (ESI (LC/MS positive mode) m/z 685 (M+H); Rt 3.40 min.) was synthesized by the synthesis similar to that of No

Sources & evidence

ORD record
ord-0bda93bd46e046159835d68484973cba
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…