Methanol → (2-tert-Butoxycarbonylamino-4-tert-Butyl-5-mercapto-phenyl)-carbamic Acid Tert-Butyl Ester

HRID 23489Notes

Reaction equation

HRID 23489 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([S:14]C#N)[C:11]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][C:9]=1[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH3:4])([CH3:3])[CH3:2].S.[Na].[BH4-].[Na+].CO>CC(O)=O.O>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[C:12]([SH:14])[C:11]([C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:10][C:9]=1[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86586439Sodium hydrogen sulphideHCID 86592609(2-tert-Butoxycarbonylamino-4-tert-Butyl-5-thiocyanato-phenyl)-carbamic Acid Tert-Butyl Ester

Product 1

HCID 54379200(2-tert-Butoxycarbonylamino-4-tert-Butyl-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-butoxycarbonylamino-4-tert-butyl-5-thiocyanato-phenyl)-carbamic acid tert-butyl ester (prepared in Example SS-2; 18 g, 43 mmol), sodium hydrogen sulfide (7.2 g, 128 mmol), sodium borohydride (9.7 g, 256 mmol), MeOH (150 mL), H2O (50 mL), and AcOH (10 mL). The crude product was used without purification.

Workup

  1. customThe crude product was used without purification

Sources & evidence

ORD record
ord-e5e7d7d137294d78b3f23a90ae62dc25
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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