Methanol → thiazol-5-ylmethyl N-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-[[(2S)-2-[(2-isopropylthiazol-4-yl)methoxycarbonylamino]-3-methyl-butanoyl]amino]-5-thiazol-5-yl-pentyl]carbamate

HRID 1939816Notes

Reaction equation

HRID 1939816 reaction equation
[NH2:1][C@H:2]([CH2:24][C:25]1[S:29][CH:28]=[N:27][CH:26]=1)[CH2:3][C@H:4]([OH:23])[C@@H:5]([NH:13][C:14]([O:16][CH2:17][C:18]1[S:22][CH:21]=[N:20][CH:19]=1)=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:30]([C:33]1[S:34][CH:35]=[C:36]([CH2:38][O:39][C:40]([NH:42][C@H:43]([C:47](O)=[O:48])[CH:44]([CH3:46])[CH3:45])=[O:41])[N:37]=1)([CH3:32])[CH3:31].CO>ClCCl>[CH:30]([C:33]1[S:34][CH:35]=[C:36]([CH2:38][O:39][C:40]([NH:42][C@H:43]([C:47]([NH:1][C@H:2]([CH2:24][C:25]2[S:29][CH:28]=[N:27][CH:26]=2)[CH2:3][C@H:4]([OH:23])[C@@H:5]([NH:13][C:14]([O:16][CH2:17][C:18]2[S:22][CH:21]=[N:20][CH:19]=2)=[O:15])[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:48])[CH:44]([CH3:46])[CH3:45])=[O:41])[N:37]=1)([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 10542235HCID 10542235, compoundHCID 15850561HCID 15850561, compound

Product 1

HCID 482967thiazol-5-ylmethyl N-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-[[(2S)-2-[(2-isopropylthiazol-4-yl)methoxycarbonylamino]-3-methyl-butanoyl]amino]-5-thiazol-5-yl-pentyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure of Example 1U but replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-5-amino-1-phenyl-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-6-(5-thiazolyl)-3-hydroxyhexane and replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with N-((2-isopropyl-4-thiazolyl)methoxycarbonyl)valine provided, after silica gel chromatography using 10% methanol in dichloromethane, 25 mg (76%) of the desired compound (Rf 0.47, 10% methanol in dichloromethane). Mass spectrum: (M+H)+ =715.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-3250baa293724dc1acc13a16f792cb0e
Source dataset
uspto-grants-1997_12
Patent number
US05696270

Reaction notes

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