4-Bromobutyryl chloride → HCID 11641483, compound

HRID 1278785Notes

Reaction equation

HRID 1278785 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:22][C:16]3([CH3:23])[CH2:17][C:18]([OH:21])([CH2:20][C:14]([CH3:24])([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:22][C:16]3([CH3:23])[CH2:17][C:18]([O:21][C:29]([CH2:28][CH2:27][CH2:26][Br:25])=[O:30])([CH2:20][C:14]([CH3:24])([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702254-Bromobutyryl chlorideHCID 11674324HCID 11674324, compound

Product 1

HCID 11641483HCID 11641483, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(benzyloxy-carbonyl)amino-3,5-dimethyl-7-hydroxyadamantane (100 mg) in DMF (0.4 mL) was added 4-bromobutyryl chloride (0.3 mL). The reaction mixture was stirred for 2 h at room temperature. The mixture was purified by thin layer chromatography eluting with ethyl acetate and hexane (½, v/v) to afford an oily product. 1H NMR (DMSO-d6, ppm): 7.38-7.29 (m, 5 H, C6H5), 7.12 (brs, 1 H, NH), 4.95 (s, 2 H, OCH2), 3.53-3.49 (t, 2 H, J=6.6 Hz, COCH2), 2.36-2.32 (t, 2 H, J=7.7 Hz, CH2Br), 2.10 (s, 2 H), 2.00-1.96 (m, 2 H, CHCH2CH2), 1.66 (s, 4 H), 1.59-1.41 (dd, 4 H, J=11.5, 51.7 Hz), 1.08-1.07 (d, 2 H, J=3.8 Hz), 0.87 (s, 6 H, 2×CH3).

Workup

  1. customThe mixture was purified by thin layer chromatography
  2. washeluting with ethyl acetate and hexane (½, v/v)
  3. customto afford an oily product

Sources & evidence

ORD record
ord-33491d2bff1e4ddfac764cae1a4ef6ed
Source dataset
uspto-grants-2002_09
Patent number
US06444702B1

Reaction notes

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