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

HRID 447150ノート

反応式

HRID 447150 の反応式
[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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-11e2ceacdd0542b1925fef49ef7b9f5c
出典データセット
uspto-grants-2013_07
特許番号
US08481547B2

反応ノート

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