Methanol → (2-tert-Butyoxycarbonylamino-4-isopropyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester

HRID 23488Notes

Reaction equation

HRID 23488 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[C:12]([S:14]C#N)[C:11]([CH:17]([CH3:19])[CH3:18])=[CH:10][C:9]=1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:4])([CH3:3])[CH3:2].S.[Na].[BH4-].[Na+].CO>CC(O)=O.O>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[C:12]([SH:14])[C:11]([CH:17]([CH3:18])[CH3:19])=[CH:10][C:9]=1[NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86586439Sodium hydrogen sulphideHCID 131723782(2-tert-Butyoxycarbonylamino-4-isopropyl-5-thiocyanato-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 131723783(2-tert-Butyoxycarbonylamino-4-isopropyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The title compound was prepared according to General Method 14b using (2-tert-butyoxycarbonylamino-4-isopropyl-5-thiocyanato-phenyl)-carbamic acid tert-butyl ester (prepared in Example SS-1; 9 g, 22 mmol), sodium hydrogen sulfide (3.7 g, 66 mmol), sodium borohydride (5.02 g, 132 mmol), MeOH (20 mL), H2O (5 mL), and AcOH (2 mL). The crude product was used without any purification. MS(APCI): 381 (M−H).

Workup

  1. customThe crude product was used without any purification

Sources & evidence

ORD record
ord-3bda13cbbbd54b98a89ab78ac315f90b
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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