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

HRID 1859562Notes

Reaction equation

HRID 1859562 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-0da423eeda014e70862f8454f5013d86
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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