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

HRID 447150Notes

Reaction equation

HRID 447150 reaction equation
[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

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-11e2ceacdd0542b1925fef49ef7b9f5c
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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