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Methanamine, N-methoxy-, hydrochloride (1:1) → (RS)-[2-(4-Benzyloxy-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 852876
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HRID 852876 반응식
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:26](O)=[O:27])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:64][O:65][NH:66][CH3:67].Cl>CN(C=O)C>[C:33]([O:32][C:30](=[O:31])[NH:29][CH:25]([C:26](=[O:27])[N:66]([O:65][CH3:64])[CH3:67])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:19][CH:20]=1)([CH3:35])([CH3:34])[CH3:36]
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참가 물질

6

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 294897Boc-O-benzyl-D-tyrosine

생성물 1

HCID 23001393(RS)-[2-(4-Benzyloxy-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester수율 100.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIPEA (28.2 ml, 20.9 g, 162 mmol) was added to a stirred solution of (RS)-3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (20.0 g, 53.9 mmol), BOP (25.00 g, 56.5 mmol) and MeONHMe.HCl (5.52 g, 56.6 mmol) in DMF (300 mL). After stirring 2 hr, the DMF was evaporated and the residue was dissolved in EtOAc and washed with water, 5% aq. HCl, saturated aq. NaHCO3 and brine, then dried with Na2SO4 and evaporated to afford (RS)-[2-(4-Benzyloxy-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (22.39 g, 100%), mp 107.1-108.7° C. 1H NMR (CDCl3) δ 0.40 (s, 9H), 2.83 (dd, J=6.2, 14.2 Hz, 1H), 3.00 (dd, J=6.1, 13.6 Hz, 1H), 3.17 (s, 3H), 3.65 (s, 3H), 4.91 (br s, 1H), 5.04 (s, 2H), 5.15 (br d, J=7.1 Hz, 1H), 6.90 (d, J=8.6 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H), 7.32-7.44 (m, 5H). 13C NMR (CDCl3) δ 172.3, 157.7, 155.2, 137.1, 130.4, 128.9, 128.5, 127.9, 127.4, 114.7, 79.6, 70.0, 61.5, 51.6, 38.0, 32.1, 28.3.

후처리

  1. customthe DMF was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water, 5% aq. HCl, saturated aq. NaHCO3 and brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-70f7412d8aca469aae101f9863d2b7d6
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253194B2

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