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

HRID 447150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447150
[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

Komponenten

8

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-11e2ceacdd0542b1925fef49ef7b9f5c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481547B2

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