2-Butene, 1-bromo-3-methyl- → HCID 15549534, compound

HRID 2299888Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH2:16][C:17]([NH:20][C:21](=[O:29])[C@@H:22]([NH:27][CH3:28])[CH2:23][CH:24]([CH3:26])[CH3:25])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:35](N(C(C)C)CC)(C)C.BrC[CH:46]=[C:47]([CH3:49])[CH3:48]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:30][CH:31]=[C:32]([CH3:33])[CH3:34])[CH2:16][C:17]([NH:20][C:21](=[O:29])[C@@H:22]([N:27]([CH3:35])[CH2:28][CH:46]=[C:47]([CH3:49])[CH3:48])[CH2:23][CH:24]([CH3:26])[CH3:25])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-4-Methyl-2-methylamino-pentanoic acid {2-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-1,1-dimethyl-ethyl}-amide (XIIa, 0.14 g, 0.31 mmol) was dissolved in THF (10 mL), treated with diisopropylethylamine (0.31 g, 2.4 mmol), and 4-bromo-2-methyl-2-butene (0.6 mmol), and heated to 50° C. for 15 hours. The reaction was concentrated and chromatographed on silica gel eluting with 2:1 hexane/EtOAc to yield the desired product.

Workup

concentrationThe reaction was concentrated
customchromatographed on silica gel eluting with 2:1 hexane/EtOAc

Sources & evidence

ORD record: ord-7358a01f7e5d4dd0aa6d3f95b9cc049b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495715B2

Reaction notes

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