p-Toluenesulfonic acid monohydrate → ((S)-5-benzyloxy-1-hydroxymethyl-3,3-dimethyl-pentyl)-carbamic acid tert-butyl ester

HRID 863239Notes

Reaction equation

HRID 863239 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:28])([CH3:27])[CH2:12][C@H:13]1[CH2:17][O:16]C(C)(C)[N:14]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(C(OCC)=O)C1)=O)CCC>CO>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:28])([CH3:27])[CH2:12][C@H:13]([NH:14][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 228824894(S)-(4-benzyloxy-2,2-dimethylbutyl)-3-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidineHCID 1317205115(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 22882578((S)-5-benzyloxy-1-hydroxymethyl-3,3-dimethyl-pentyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is prepared starting from 75.2 g of 4(S)-(4-benzyloxy-2,2-dimethylbutyl)-3-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidine and 2.0 g of p-toluenesulfonic acid hydrate in 500 ml of methanol analogously to Example 20a): Rf (A)=0.31; FAB-MS: (M+H)+ =352; anal. calc. for C20H33NO4 : C68.34%, H9.46%, N3.99%; found C68.14%, H9.37%, N3.98%.

Sources & evidence

ORD record
ord-2a92133a016c4f5a8a8338b437e13201
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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