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Benzoyl chloride → benzyl N-benzoyl-(L)-pyroglutamate

HRID 543255
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HRID 543255 반응식
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[H-].[Na+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[C:19]([N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 2381219Benzyl 5-oxoprolinate

생성물 1

HCID 13655564benzyl N-benzoyl-(L)-pyroglutamate수율 70%

시약·촉매·용매 1

HCID 241Benzene용매3회

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온도
55 °C

실험 절차

A solution of 21.9 g (0.1 mol) of benzyl (L)-pyroglutamate (prepared according to Example II(1)) in 150 ml of benzene is added over an hour to a suspension of 4.8 g (0.1 mol) of sodium hydride in 15 ml of dry benzene. The mixture is stirred for one hour at ordinary temperature and 14.1 g (0.1 mol) of benzoyl chloride diluted in benzene are then introduced. The reaction mixture is stirred for 4 hours at 55° C. and then for 18 hours at ordinary temperature. After the mixture has been washed with water, the solvent evaporated off and the residue taken up with ether, white crystals of melting point=101°/2° C. are obtained; yield=70%; Rf=0.68 (A).

후처리

  1. additionare then introduced
  2. waitfor 18 hours at ordinary temperature
  3. washAfter the mixture has been washed with water
  4. customthe solvent evaporated off
  5. customtaken up with ether, white crystals of melting point=101°/2° C.
  6. customare obtained

출처 및 근거

ORD 기록
ord-dade466880d54c7fa19f26a9a55fbb81
출처 데이터셋
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04661512

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