Acetyl chloride → HCID 67495230, compound

HRID 1776020Notes

Reaction equation

HRID 1776020 reaction equation
[CH3:1][C@@:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][NH:3]1.[C:10](Cl)(=[O:12])[CH3:11].C(N(CC)C(C)C)(C)C>CN(C)C(=O)C>[C:10]([N:3]1[CH2:4][CH2:5][CH2:6][C@@:2]1([CH3:1])[C:7]([OH:9])=[O:8])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 69936642-Methyl-L-proline

Product 1

HCID 67495230HCID 67495230, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of (S)-2-methyl-pyrrolidine-2-carboxylic acid (50.0 mg, 0.387 mmol) dissolved in N,N-dimethylacetamide (1.5 mL, 16 mmol) was added a solution of acetyl chloride (31.9 mg, 0.406 mmol) dissolved in N,N-dimethylacetamide (0.5 mL), and then N,N-diisopropylethylamine (1 mL, 6 mmol) was added and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was concentrated to produce the title compound as a light brown oil (30 mg, 40% yield). (m/z): [M+H]+ calcd for C8H11NO3 172.10 found 172.2.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-84c1558c4f4e43c09e3310a31b5005ed
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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