Acetyl chloride → HCID 69063309, compound

HRID 1864500Notes

Reaction equation

HRID 1864500 reaction equation
[C:1]([Cl:4])(=O)[CH3:2].[OH:5][C@H:6]1[CH2:10][CH2:9][NH:8][C@@H:7]1[C:11]([OH:13])=[O:12]>>[ClH:4].[OH:5][C@H:6]1[CH2:10][CH2:9][NH:8][C@@H:7]1[C:11]([O:13][CH2:1][CH3:2])=[O:12]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 440575trans-3-hydroxy-L-proline

Product 1

HCID 69063309HCID 69063309, compound

Conditions

Temperature
100 °C

Procedure

Acetyl chloride (10.8 mL, 153 mmol) was slowly added to ice cold 100% Ethanol (100 mL). (3S)-3-hydroxy-L-proline (5 g, 38.2 mmol) was added and heated at 100° C. for 16 hours. The ester was concentrated to a solid and used without purification. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (t, J=8.1 Hz, 3H), 1.9 (m, 2H), 3.3 (m, 2H), 4.1 (m, 1H), 4.2 (q, J=7.1 Hz, 2H) 4.4 (m, 1H), 9.0 (s, 1H), 10.4 (s, 1H).

Workup

  1. concentrationThe ester was concentrated to a solid
  2. customused without purification

Sources & evidence

ORD record
ord-853d26aa4c714897a876411526f38a36
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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