L-Tryptophan → N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester

HRID 1634916

반응식

HRID 1634916 반응식
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:23]([OH:25])=[O:24])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C@H](C(O)=O)[CH2:28][C:29]1[C:37]2C(=CC=CC=2)N[CH:30]=1.C(Cl)(OCC1C=CC=CC=1)=O.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+].C(Br)(C)(C)C>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC(N(C)C)=O>[CH3:28][C:29]([O:24][C:23](=[O:25])[C@H:12]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10])([CH3:37])[CH3:30]

참가 물질

10

반응물 6

HCID 6305L-TryptophanHCID 10387Benzyl chloroformateHCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 101176benzyloxycarbonyl-L-tryptophan

생성물 1

HCID 15600488N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester수율 99%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매2회HCID 31374Dimethylacetamide용매

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온도
55 °C

실험 절차

To a suspension of N-[(phenylmethoxy)carbonyl]-L-tryptophan (33.27 g; 98.32 mol) (previously prepared by reacting L-tryptophan with CBZCl, in H2O and 1N NaOH), benzyltriethylammonium chloride (BTEAC) (22.4 g; 98.32 mol) and K2CO3 (176.91 g; 1.28 mol) in dimethylacetamide (750 mL) is added tert-butyl bromide (265 mL; 2.36 mol). The solution is heated to 55° C. and vigorously stirred for 19 hours. The mixture is then cooled to room temperature, diluted with H2O (3L) and then extracted with EtOAc (2×1L). The organic phases are evaporated to dryness to obtain the title product as a pale yellow oil (36 g; 98 mol)

후처리

  1. custompreviously prepared
  2. temperatureThe mixture is then cooled to room temperature
  3. extractionextracted with EtOAc (2×1L)
  4. customThe organic phases are evaporated to dryness

출처 및 근거

ORD 기록
ord-7abfc88921c243fe8a28fbfcf4ce1e90
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509324B1

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