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

HRID 72243Notes

Reaction equation

HRID 72243 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:18]=[O:19])=[CH:8][C:9]=1[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:18][OH:19])=[CH:8][C:9]=1[NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[O:4]

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

To a suspension of 3-tert-butoxycarbonylamino-5-formyl-thiophene-2-carboxylic acid methyl ester (1.49 g) in ethanol/water (95 mL/95 mL) sodiumborohydride (105.8 mg) was added at 0° C. The mixture was stirred for 1 h at this temperature. Then ethyl acetate and water were added. The aqueous phase was extracted several times with ethyl acetate, the combined organic phases dried over sodium sulfate and the solvent removed in vacuo. The product with the molecular weight of 287.33 (C12H17NO5S) was obtained in this way; MS (ESI): 288 (M+H+).

Workup

  1. additionwas added at 0° C
  2. extractionThe aqueous phase was extracted several times with ethyl acetate
  3. dry with materialthe combined organic phases dried over sodium sulfate
  4. customthe solvent removed in vacuo
  5. customThe product with the molecular weight of 287.33 (C12H17NO5S) was obtained in this way

Sources & evidence

ORD record
ord-fc92f90ec587461e8b59514728325fb6
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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