Triethylamine → (R,E)-ethyl 3-(benzyloxycarbonylamino)-3-(3-(4-(4-bromo-2,6-dimethylphenyl)but-2-enamido)phenyl)propanoate

HRID 735636Notes

Reaction equation

F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Br:28][C:29]1[CH:34]=[C:33]([CH3:35])[C:32]([CH2:36]/[CH:37]=[CH:38]/[C:39]([OH:41])=O)=[C:31]([CH3:42])[CH:30]=1.[NH2:43][C:44]1[CH:45]=[C:46]([C@H:50]([NH:57][C:58]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:59])[CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH:47]=[CH:48][CH:49]=1.C(N(CC)CC)C>C(#N)C>[CH2:61]([O:60][C:58]([NH:57][C@@H:50]([C:46]1[CH:47]=[CH:48][CH:49]=[C:44]([NH:43][C:39](=[O:41])/[CH:38]=[CH:37]/[CH2:36][C:32]2[C:31]([CH3:42])=[CH:30][C:29]([Br:28])=[CH:34][C:33]=2[CH3:35])[CH:45]=1)[CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])=[O:59])[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

Conditions

Temperature: 0 °C

Procedure

BOP (1.3 g, 3.0 mmol) was added to a solution of 53C (675 mg, 2.5 mmol), 39C (1.0 g, 2.75 mmol) and triethylamine (5.0 mmol) in acetonitrile (25 mL) at 0° C. The mixture was stirred at 0° C. for 2 h and at ambient temperature for 15 h. The mixture was concentrated in vacuo and purified by flash chromatography (0% to 60% EtOAc in hexanes) to afford 53D (800 mg, 54%) as a white solid. MS (ESI) m/z 593.3/595.3 (M+H)+.

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by flash chromatography (0% to 60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-59229cda631c4d779039754adac8b4dd
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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