(S)-1-Phenyl-3-propanolamine → (2S)-N-[(1S)-3-hydroxy-1-phenylpropyl]-3-[(4-tert-pentylphenyl)sulfonyl]-1,3-thiazolidine-2-carboxamide

HRID 1964816Notes

Reaction equation

HRID 1964816 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:19][CH2:18][S:17][CH:16]2[C:20]([OH:22])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[NH2:23][C@H:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][CH2:26][OH:27]>>[OH:27][CH2:26][CH2:25][C@H:24]([NH:23][C:20]([C@H:16]1[N:15]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])=[CH:11][CH:10]=2)(=[O:13])=[O:14])[CH2:19][CH2:18][S:17]1)=[O:22])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 2734520(S)-1-Phenyl-3-propanolamineHCID 68623277HCID 68623277, compound2×

Product 1

HCID 57462299(2S)-N-[(1S)-3-hydroxy-1-phenylpropyl]-3-[(4-tert-pentylphenyl)sulfonyl]-1,3-thiazolidine-2-carboxamide

Procedure

Following the general strategies and protocols outlined in Example 1, starting from 3-[(4-tert-pentylphenyl)sulfonyl]-1,3-thiazolidine-2-carboxylic acid (Intermediate 8) and commercial (3S)-3-amino-3-phenyl-1-propanol, the title compound was obtained in 99% purity by HPLC.

Sources & evidence

ORD record
ord-bb98d9dfce334673abd918c39224dd97
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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