Water → 3-Tert-butoxycarbonylamino-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

HRID 532448Notes

Reaction equation

HRID 532448 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH:20]=[O:21])=[CH:10][C:11]=1[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:6].C(OCC)(=O)C.O>C(O)C.O>[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH2:20][OH:21])=[CH:10][C:11]=1[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86628784HCID 86628784, compound

Product 1

HCID 689407663-Tert-butoxycarbonylamino-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Sodium borohydride was added to a suspension of 3-tert-butoxycarbonylamino-5-formylthiophene-2-carboxylic acid methyl ester (1.5 g) in ethanol/water (95 mL/95 mL) at 0° C. The reaction was then stirred at this temperature for 1 h. Then ethyl acetate and water were added, and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The product with the molecular weight of 287.34 (C12H17NO5S) was obtained in this way; MS (ESI): 288 (M+H+).

Workup

  1. extractionthe aqueous phase was extracted several times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 287.34 (C12H17NO5S) was obtained in this way

Sources & evidence

ORD record
ord-60e95aebc2e443799327ece7a62e8d1a
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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