Triethylamine → (S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

HRID 447150노트

반응식

HRID 447150 반응식
[N:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5]C[CH2:3][CH2:2]1.O.O[N:18]1C2C=CC=CC=2N=N1.[C:27]([NH:34][C@H:35]([C:42]([OH:44])=O)[CH2:36][C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.C(Cl)(Cl)Cl>[O:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[C:7]1[N:1]1[CH2:6][CH2:5][N:18]([C:42](=[O:44])[C@@H:35]([NH:34][C:27](=[O:28])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:36][C:37]2[S:38][CH:39]=[CH:40][CH:41]=2)[CH2:3][CH2:2]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 76106Benzoxazole, 2-(1-piperidinyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27344843-(Thien-2-yl)-L-alanine, N-BOC protectedHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 67235987(S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

2-Piperidino-1,3-benzoxazole (203.6 mgs, 1.00 mmol), N-hydroxybenzotriazole hydrate (138.2 mg, 1.02 mmol) and Boc-β-(2-thienyl)-L-alanine (272.6 mgs, 1.00 mmol) in dichloromethane (10 mL) was cooled in an ice bath, then treated with triethylamine (0.30 mL, 2.15 mmol) and 1-[3-dimethylaminopropyl]-3-ethyl carbodiimide hydrochloride (199.5 mg, 1.04 mmol). The resulting mixture was stirred overnight at room temperature. After 18 h, the resulting mixture was diluted with chloroform and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to a residue. The residue was purified by flash column chromatography, eluting with 3% methanol in chloroform to yield (S)-tert-butyl 1-(4-(benzo[d]oxazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate as a colorless glass.

후처리

  1. waitAfter 18 h
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a residue
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 3% methanol in chloroform

출처 및 근거

ORD 기록
ord-11e2ceacdd0542b1925fef49ef7b9f5c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481547B2

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