Acetyl chloride → HCID 66618321, compound

HRID 1009974Notes

Reaction equation

HRID 1009974 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([O:17][C:18](=[O:29])[C@@H:19]([NH2:28])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[CH:12]1([O:17][C:18](=[O:29])[C@@H:19]([NH:28][C:37](=[O:39])[CH3:38])[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 86636735HCID 86636735, compound

Product 1

HCID 66618321HCID 66618321, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To (S)-2-Amino-3-p-tolyl-propionic acid cyclopentyl ester p-toluenesulfonic acid salt prepared in the above stage (10 g, 0.022 mol) was added dichloromethane 200 ml) under nitrogen. Triethylamine (6.29 ml, 0.044 mol) was added dropwise with stirring. Acetyl chloride (1.72 ml, 0.022 mol) in dichloromethane (50 ml) was added dropwise to the reaction. Acetyl chloride (0.1 ml) in DCM (0.5 ml) was added after 20 mins and the reaction reached completion after 1 hr. The organic phase was washed with saturated sodium bicarbonate (3×200 ml), dried (Na2SO4) and the solvent removed in vacuo. The required product was obtained 6.62 g, 93% yield and was used in the next step without further purification. m/z 321 [M++H]+

Workup

  1. customafter 1 hr
  2. washThe organic phase was washed with saturated sodium bicarbonate (3×200 ml)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6fc2039d94784ce58589f47fd7320d9b
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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