methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate → (E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-carboxy-ethylcarbamoyl]-2-(2,2-difluoro-ethyl)-2-hydroxy-12-oxo-nonadec-4-enoic acid

HRID 1779217Notes

Reaction equation

HRID 1779217 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@:22]([CH2:27][CH:28]([F:30])[F:29])([OH:26])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].N[C@@H](CC1C=CC(OCCCC)=CC=1)C(OC(C)(C)C)=O.N[C@@H](CC1C=CC(OCCCC)=CC=1)C(OC)=O>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@:22]([CH2:27][CH:28]([F:30])[F:29])([OH:26])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 68030835methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionateHCID 118157889(E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(2,2-difluoro-ethyl)-2-hydroxy-12-oxo-nonadec-4-enoic acidHCID 131734865tert-butyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate

Product 1

HCID 118157849(E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-carboxy-ethylcarbamoyl]-2-(2,2-difluoro-ethyl)-2-hydroxy-12-oxo-nonadec-4-enoic acid

Procedure

The title compound was synthesized by a method similar to that of No. 5509214, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(2,2-difluoro-ethyl)-2-hydroxy-12-oxo-nonadec-4-enoic acid, except that tert-butyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate was used instead of No. 5509214, methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate.

Sources & evidence

ORD record
ord-a31d5709e4174a18ad0127547e124766
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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