Ethyl chloroformate → Cetilistat

HRID 747562Notes

Reaction equation

HRID 747562 reaction equation
[CH2:1]([O:17][C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ClC(OCC)=O>N1C=CC=CC=1>[CH2:1]([O:17][C:18]1[O:24][C:23](=[O:25])[C:22]2[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:21]=2[N:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 11697437HCID 11697437, compound

Product 1

HCID 9952916CetilistatYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4.0 g (10.0 mmol) of 2-hexadecyloxycarbonylamino-5-methylbenzoic acid are introduced into 20 ml of pyridine at 0° C. under a nitrogen atmosphere, and 4.93 g (45.4 mmol) of ethyl chloroformate are added dropwise to the resulting solution at 0° C. over the course of 20 min. After the reaction mixture has been stirred at 0° C. for 1 h and at room temperature for 2 h it is added to 30 ml of ice-water. The solid is filtered off and dried in vacuo. 3.3 g (8.2 mmol, 82%) of 2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one are obtained in the form of a pale yellow coloured solid with a melting point of 67° C. (literature: 72-73° C., WO 00/40569).

Workup

  1. filtrationThe solid is filtered off
  2. customdried in vacuo

Sources & evidence

ORD record
ord-360836595222496ca6443257e485a827
Source dataset
uspto-grants-2008_07
Patent number
US07396952B2

Reaction notes

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