Bromotrichloromethane → HCID 18517860, compound

HRID 1368958Notes

Reaction equation

HRID 1368958 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:13]([NH:15][CH:16]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:17]([C:19]1[O:20][CH2:21][CH:22]([C:24]([O:26][CH3:27])=[O:25])[N:23]=1)[OH:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.BrC(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:13]([NH:15][CH:16]([CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH:17]([C:19]1[O:20][CH:21]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[N:23]=1)[OH:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18517881HCID 18517881, compound

Product 1

HCID 18517860HCID 18517860, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution comprised of methyl 2-[2-(2-benzyloxycarbonylamino-4-methylvalerylamino)-1-hydroxy-4-phenylbutyl]-4,5-dihydrooxazole-4-carboxylate (0.036 g, 0.067 mmol) in methylene chloride (3 mL) was cooled to 0° C. and then DBU (11.2 mg, 72.7 μmol) and bromotrichloromethane (14.6 mg, 73.7 μmol) were added. The mixture was stirred for 6 hours at room temperature and concentrated. The residue was dissolved in ethyl acetate (20 mL) and the solution was dried (MgSO4) and concentrated. The product was purified from the residue by flash chromatography eluting with 1:3 hexanes/ethyl acetate to provide methyl 2-[2-(2-benzyloxycarbonylamino-4-methylvalerylamino)-1-hydroxy-4-phenylbutyl]oxazole-4-carboxylate (12 mg, 0.022 mmol) as a white solid. MS(PCI) m/z=538 (M+1) 1H NMR (CDCl3): δ 0.8-1.05 (d, J=4 Hz, 6H), δ 1.55-1.70 (m, 3H), δ 2.00 (m, 1H), δ 2.40 (m, 1H), δ 2.69 (m, 2H), δ 3.99 (m, 3H) 4.45 (m, 1H), δ 5.17 (s, 2H), δ 5.78 (m, 1H, δ 7.01 (d, J=4 Hz 1H), δ 7.14-7.47 (m, 10H) 7.72(d, J=4 Hz, 1H), δ 8.40 (s, 1H). (C29H35N3O7).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  3. dry with materialthe solution was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe product was purified from the residue by flash chromatography
  6. washeluting with 1:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-a58b96e0e8b146818042d0c78318e764
Source dataset
uspto-grants-2003_06
Patent number
US06576630B1

Reaction notes

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