N-((N-methyl-N-((2-(1-pyrrolidinyl)-4-thiazolyl)methyl)amino)carbonyl)-L-valine → 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2-methyl-5-(1-methylethyl)-3,6-dioxo-8,11-bis(phenylmethyl)-1-(2-(1-pyrrolidinyl)-4-thiazolyl)-, 5-isoxazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))-

HRID 1736071Notes

Reaction equation

HRID 1736071 reaction equation
[CH3:1][N:2]([C:14]([NH:16][C@H:17]([C:21]([OH:23])=O)[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:3][C:4]1[N:5]=[C:6]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[S:7][CH:8]=1.[NH2:24][C@@H:25]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:26][C@H:27]([OH:46])[C@@H:28]([NH:36][C:37]([O:39][CH2:40][C:41]1[O:45][N:44]=[CH:43][CH:42]=1)=[O:38])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:1][N:2]([C:14]([NH:16][C@H:17]([C:21]([NH:24][C@@H:25]([CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[CH2:26][C@H:27]([OH:46])[C@@H:28]([NH:36][C:37]([O:39][CH2:40][C:41]1[O:45][N:44]=[CH:43][CH:42]=1)=[O:38])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:23])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH2:3][C:4]1[N:5]=[C:6]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[S:7][CH:8]=1

Participants

3

Reactant 2

HCID 54281443N-((N-methyl-N-((2-(1-pyrrolidinyl)-4-thiazolyl)methyl)amino)carbonyl)-L-valineHCID 57164722(2S,3S,5S)-5-amino-2-(N-((5-isoxazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

Product 1

HCID 4829522,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2-methyl-5-(1-methylethyl)-3,6-dioxo-8,11-bis(phenylmethyl)-1-(2-(1-pyrrolidinyl)-4-thiazolyl)-, 5-isoxazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))-

Procedure

Using the procedure of Example 1U, but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with N-((N-methyl-N-((2-(1-pyrrolidinyl)-4-thiazolyl)methyl)amino)carbonyl)-L-valine and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-5-amino-2-(N-((5-isoxazolyl)methoxy-carbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after purification by silica gel chromatography using 2% methanol in chloroform, the desired compound (Rf 0.30, 4% methanol in chloroform).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-a6d6c0ace2c14c04b99b542f3edef6f7
Source dataset
uspto-grants-1996_07
Patent number
US05539122

Reaction notes

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