Water → HCID 22726835, compound

HRID 2085971Notes

Reaction equation

HRID 2085971 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:19]C#N)=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1.[BH4-].[Na+].O>CO>[NH2:1][C:2]1[S:3][C:4]([SH:19])=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22726737HCID 22726737, compound

Product 1

HCID 22726835HCID 22726835, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-amino-4-(2-t-butyloxycarbonylaminoethylthiomethyl)-5-thiocyanato-1,3-thiazole (2.83 g, 8.19 mmol) in methanol (30 mL) at room temperature was added sodium borohydride under nitrogen (0.93 g, 24.6 mol) and stirring was continued for 1 hour. After addition of water, stirring was continued until gas evolution subsided and the aqueous solution was washed with methylene chloride to remove impurities. Aqueous thiolate solution was neutralized with dilute hydrochloric acid and the product was extracted with ethyl acetate (all manipulations were performed under nitrogen to prevent formation of disulfide). Organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford pale orange foam of title product (1.72 g) which was used f6r further steps without further purification. 1H NMR (CDCl3) δ 1.40 (s, 9H), 2.60 (m, 2H), 3.20 (m, 2H), 3.65 (s, 2H), 5.40 (s, 1H).

Workup

  1. stirringstirring
  2. washthe aqueous solution was washed with methylene chloride
  3. customto remove impurities
  4. extractionthe product was extracted with ethyl acetate (all manipulations were performed under nitrogen to prevent formation of disulfide)
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f27eb1aba1db4af5b38118cc714f4488
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

Loading…