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

HRID 1859561Notes

Reaction equation

HRID 1859561 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-062b650b1d6846a5adefa4dcec6f1a09
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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