Methanol → HCID 43577519, compound

HRID 424629Notes

Reaction equation

HRID 424629 reaction equation
[CH:1]1([N:4]([CH2:17][C:18](O)=[O:19])[S:5]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])(=[O:7])=[O:6])[CH2:3][CH2:2]1.CO>C1COCC1>[Cl:14][C:13]1[CH:12]=[C:11]([Cl:15])[CH:10]=[C:9]([Cl:16])[C:8]=1[S:5]([N:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:17][CH2:18][OH:19])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 60828526HCID 60828526, compound

Product 1

HCID 43577519HCID 43577519, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M soln. of borane-dimethylsulfide complex in THF (4.96 ml, 9.92 mmol) was added to a soln. of [cyclopropyl-(2,4,6-trichlorobenzenesulfonyl)-amino]-acetic acid (1.77 g, 4.96 mmol) in anhydrous THF (30 ml) and the mixture was stirred for 1 h, while cooling with ice. The reaction mixture was stirred at RT for approx. 18 h, MeOH (2 ml) was then cautiously added and the mixture was concentrated i. vac. MeOH was repeatedly added to the residue and the mixture concentrated i. vac. 5% strength NaHCO3 soln. was added to the crude product, the mixture was extracted with EtOAc and the organic phase was dried with Na2SO4 and concentrated i. vac. Yield: 1.02 g (60%)

Workup

  1. temperaturewhile cooling with ice
  2. concentrationthe mixture was concentrated i
  3. additionMeOH was repeatedly added to the residue
  4. concentrationthe mixture concentrated i
  5. additionwas added to the crude product
  6. extractionthe mixture was extracted with EtOAc
  7. dry with materialthe organic phase was dried with Na2SO4
  8. concentrationconcentrated i

Sources & evidence

ORD record
ord-6b82f1042f78471b92eacf78dc4123fc
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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