Tert-Butylamine → (S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

HRID 1276422노트

반응식

HRID 1276422 반응식
[C:1]([NH:8][C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.[C:37]([NH2:41])([CH3:40])([CH3:39])[CH3:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:25](=[O:26])[NH:41][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:16]=1)([CH3:5])([CH3:7])[CH3:6]

참가 물질

7

반응물 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 15517726(S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester수율 96.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N-Boc-O-Benzyl-tyrosine (20.0 g, 53.9 mmol) was dissolved in DMF (270 mL) and treated with diisopropylethylamine (19 mL, 108 mmol), tert-butylamine (5.7 mL. 53.9 mmol), and HBTU (13.9 g, 53.9 mmol). The reaction was stirred for 15 minutes and then diluted with EtOAc (1 L), washed with saturated bicarbonate solution (2×1 L) and brine (1 L), dried over Na2SO4 and concentrated to give 22.1 g (92%) of (S)-[2-(4-Benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester.

후처리

  1. washwashed with saturated bicarbonate solution (2×1 L) and brine (1 L)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c54fd9e41660439db1afd391318c318c
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166052

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