Methanol → tert-Butyl (1(S)-hydroxymethyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

HRID 507830Notes

Reaction equation

HRID 507830 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:36]=[CH:35][CH:34]=[CH:33][C:8]=1[C:9]([NH:11][CH2:12][C@H:13]([CH:30]([CH3:32])[CH3:31])[CH2:14][C@H:15]1[CH2:19][O:18][C:17](C)(C)[N:16]1NC(OC(C)(C)C)=O)=[O:10].[OH2:37].[C:38]1([CH3:48])[CH:43]=CC(S(O)(=O)=O)=C[CH:39]=1.C[OH:50]>>[OH:18][CH2:19][C@@H:15]([NH:16][C:17](=[O:50])[O:37][C:38]([CH3:48])([CH3:43])[CH3:39])[CH2:14][C@H:13]([CH2:12][NH:11][C:9](=[O:10])[C:8]1[CH:33]=[CH:34][CH:35]=[CH:36][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:30]([CH3:31])[CH3:32]

Participants

4

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 68624344tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate

Product 1

HCID 86613453tert-Butyl (1(S)-hydroxymethyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

Procedure

The solution of 3.70 g of tert-butyl 4(S)-(2(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carbamate in 70 ml of methanol is admixed with 0.143 g of p-toluenesulphonic acid monohydrate and stirred at room temperature over 14 hours. The reaction mixture is concentrated by evaporation and the title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.16 (3:1 EtOAc-heptane); Rt=4.23 (gradient I).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-973b76ab999943b5921c32f7a7ec4150
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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