Methanol → N-[3-Hydroxy-5-({hydroxy[(1,3-thiazol-5-yl)methoxy]methylidene}amino)-1,6-diphenylhexan-2-yl]-2-[(hydroxy{[2-(morpholin-4-yl)-1,3-thiazol-4-yl]methoxy}methylidene)amino]-3-methylbutanimidic acid

HRID 1457115Notes

Reaction equation

HRID 1457115 reaction equation
[N:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][C@@H:24]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:25][C@H:26](O)[C@@H:27]([NH:35][C:36]([O:38][CH2:39][C:40]3[S:44][CH:43]=[N:42][CH:41]=3)=[O:37])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N[C@@H](CC1C=CC=CC=1)C[C@H](O)[C@@H](NC(OCC1SC=NC=1)=[O:67])CC1C=CC=CC=1.N[C@H]([C@@H](O)C[C@@H](NC(OCC1SC=NC=1)=O)CC1C=CC=CC=1)CC1C=CC=CC=1.CO>C(Cl)(Cl)Cl>[N:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][C@H:24]([C@@H:25]([OH:67])[CH2:26][C@@H:27]([NH:35][C:36]([O:38][CH2:39][C:40]3[S:44][CH:43]=[N:42][CH:41]=3)=[O:37])[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[N:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 482932N-[4-Hydroxy-5-({hydroxy[(1,3-thiazol-5-yl)methoxy]methylidene}amino)-1,6-diphenylhexan-2-yl]-2-[(hydroxy{[2-(morpholin-4-yl)-1,3-thiazol-4-yl]methoxy}methylidene)amino]-3-methylbutanimidic acidHCID 10812314(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexaneHCID 111019781,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamate

Product 1

HCID 482933N-[3-Hydroxy-5-({hydroxy[(1,3-thiazol-5-yl)methoxy]methylidene}amino)-1,6-diphenylhexan-2-yl]-2-[(hydroxy{[2-(morpholin-4-yl)-1,3-thiazol-4-yl]methoxy}methylidene)amino]-3-methylbutanimidic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 1 U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with the resultant compound of Example 11 E and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after silica gel chromatography using 2% methanol in chloroform, 196 mg (90%) of the desired compound (Rf 0.19, 4% methanol in chloroform), mp. 146°-148° C. Mass spectrum: (M+H)+ =751.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-98592aa43b1f46568e501135070cdd33
Source dataset
uspto-grants-1998_12
Patent number
US05846987

Reaction notes

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