Methanol → (2-isopropylthiazol-4-yl)methyl N-[(1S)-1-[[(1S,2S,4S)-1-benzyl-2-hydroxy-5-thiazol-5-yl-4-(thiazol-5-ylmethoxycarbonylamino)pentyl]carbamoyl]-2-methyl-propyl]carbamate

HRID 1858489Notes

Reaction equation

HRID 1858489 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][O:10][C:11]([NH:13][C@H:14]([C:18]([OH:20])=O)[CH:15]([CH3:17])[CH3:16])=[O:12])[N:8]=1)([CH3:3])[CH3:2].[NH2:21][C@H:22]([C@@H:30]([OH:49])[CH2:31][C@H:32]([NH:39][C:40]([O:42][CH2:43][C:44]1[S:48][CH:47]=[N:46][CH:45]=1)=[O:41])[CH2:33][C:34]1[S:38][CH:37]=[N:36][CH:35]=1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CO>C(Cl)(Cl)Cl>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][O:10][C:11]([NH:13][C@H:14]([C:18]([NH:21][C@H:22]([C@@H:30]([OH:49])[CH2:31][C@H:32]([NH:39][C:40]([O:42][CH2:43][C:44]2[S:48][CH:47]=[N:46][CH:45]=2)=[O:41])[CH2:33][C:34]2[S:38][CH:37]=[N:36][CH:35]=2)[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:20])[CH:15]([CH3:16])[CH3:17])=[O:12])[N:8]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 10542235HCID 10542235, compoundHCID 57028614HCID 57028614, compound

Product 1

HCID 482968(2-isopropylthiazol-4-yl)methyl N-[(1S)-1-[[(1S,2S,4S)-1-benzyl-2-hydroxy-5-thiazol-5-yl-4-(thiazol-5-ylmethoxycarbonylamino)pentyl]carbamoyl]-2-methyl-propyl]carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 1U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with N-((2-isopropyl-4-thiazolyl)methoxycarbonyl)valine and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-2-amino-1-phenyl-5-(N-((5-thiazolyl)methoxycarbonyl)amino)-6-(5-thiazolyl)-3-hydroxyhexane provided, after silica gel chromatography using 1% methanol in chloroform, 54 mg (66%) of the desired compound (Rf 0.6, 10% methanol in CH2Cl2). 1H NMR (DMSO-d6) δ 0.69 (d, 3 H), 0.74 (d, 3 H), 1.31 (d, 6 H), 1.47 (m, 2 H), 1.85 (m, 1 H), 2.75 (m, 4 H), 2.95 (m, 1 H), 3.57 (m, 1 H), 3.80 (m, 2 H), 4.08 (m, 1 H), 4.95 (d, 1 H), 5.03 (s, 2 H), 5.19 (s, 2 H), 7.12-7.29 (m), 7.45 (s, 1 H), 7.47 (s, 1 H). Mass spectrum: (M+H)+ =715.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-639d4bf05e1f4558acf035651531d52a
Source dataset
uspto-grants-2000_11
Patent number
US06150530

Reaction notes

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