Acetic Acid → HCID 57295847, compound

HRID 342136Notes

Reaction equation

HRID 342136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:20][CH2:21][S:22][CH3:23])[CH:18]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:20][CH2:21][S:22][CH3:23])[CH2:18][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1)=[O:15])([CH3:10])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 79323-ChloroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 13245620HCID 13245620, compound

Product 1

HCID 57295847HCID 57295847, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-chloroaniline (10.3 mL, 97.4 mmol), the product from Step G (23.9 g, 97.4 mmol), and acetic acid (27.8 mL, 487 mmol) in dichloroethane (250 mL) under nitrogen was added sodium triacetoxyborohydride (41.3 g, 195 mmol). The reaction was stirred overnight, then quenched with saturated sodium bicarbonate solution. The solution was diluted with CHCl3, and the organic phase was washed with water, 10% citric acid and brine. The solution was dried over sodium sulfate and concentrated in vacuo to provide the crude product (34.8 g) which was chromatographed on silica gel with 20% ethyl acetate in hexane to obtain the title compound.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. additionThe solution was diluted with CHCl3
  3. washthe organic phase was washed with water, 10% citric acid and brine
  4. dry with materialThe solution was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product (34.8 g) which
  7. customwas chromatographed on silica gel with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-090e7586f6e14e2b9f77ffbdac714040
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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