(S)-2-amino-3-(4-butoxy-phenyl)-propionamide → (E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-carbamoyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid

HRID 1779216Notes

Reaction equation

HRID 1779216 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:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]2([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])OCC[O:44]2)[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14](OC)=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:55][C@@H](CC1C=CC(OCCCC)=CC=1)C(N)=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:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:44])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([OH:25])=[O:24])=[O:20])[C:14](=[O:15])[NH2:55])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 90060237(S)-2-amino-3-(4-butoxy-phenyl)-propionamideHCID 131734849tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

Product 1

HCID 118157661(E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-carbamoyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid

Procedure

An intermediate was synthesized by a method similar to that of No. 5534988, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate, except that (S)-2-amino-3-(4-butoxy-phenyl)-propionamide was used instead of (S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide, and the title compound was obtained by a synthetic method similar to that of No. 5444958, (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid.

Workup

  1. customAn intermediate was synthesized by a method similar to that of No

Sources & evidence

ORD record
ord-e1e4f6cb3efb443f8fe425831c6c0edd
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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