N-(tert-butoxycarbonyl)glycine → Methyl 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylate

HRID 655968노트

반응식

HRID 655968 반응식
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:37][CH2:38][C:39]1([C:45]([O:47][CH3:48])=[O:46])[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:9]([O:8][C:6]([NH:1][CH2:2][C:3]([N:42]1[CH2:43][CH2:44][C:39]([CH2:38][OH:37])([C:45]([O:47][CH3:48])=[O:46])[CH2:40][CH2:41]1)=[O:5])=[O:7])([CH3:12])([CH3:11])[CH3:10]

참가 물질

6

반응물 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57920285Methyl 4-(hydroxymethyl)piperidine-4-carboxylate

생성물 1

HCID 57920289Methyl 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylate수율 98.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of Boc-Gly-OH (331 mg, 1.89 mmol, 1.1 equiv.) in DMF (1 mL) was added HBTU (718 mg, 1.89 mmol, 1.1 equiv.), followed by addition of methyl 4-(hydroxymethyl)piperidine-4-carboxylate (1.72 mmol, 1 equiv.) and DIEA (749 μL, 4.30 mmol, 2.5 equiv.) at rt. The reaction mixture was stirred for 1 h. The mixture was partitioned between EtOAc and H2O. The organic layer was washed by saturated NaHCO3, water and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by column chromatography to give methyl 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylate (560 mg, 98%, two steps). LRMS (M-Boc+H+) m/z 231.1.

후처리

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washThe organic layer was washed by saturated NaHCO3, water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-d8ccd7a71e7b4dd18be5d717a24492a3
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071625B2

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