Triethylamine → HCID 66951785, compound

HRID 1171241Notes

Reaction equation

HRID 1171241 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]([O:13][C@H:14]([CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)CC)C.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])C>ClCCl.CCCCCC>[CH2:33]([O:32][C:30]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:11]([O:13][C@H:14]([CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][C:42]([O:45][CH2:46][CH3:47])=[O:44])=[O:31])[CH3:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 66949959HCID 66949959, compound

Product 1

HCID 66951785HCID 66951785, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (1R)-2-acetyloxy-1-methylethyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (19) (8.9 g, 22.4 mmol) and ethyl chloroformate (5.30 mL, 55.3 mmol) in anhydrous dichloromethane, triethylamine (7.7 mL, 55.3 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. The solution was partitioned between dichloromethane and 10% citric acid and washed with water. The organic layer was dried over MgSO4, and concentrated to dryness. Chromatography (30% ethyl acetate in hexane) provided the title compound (20) (11.5 g, 95% yield) as a white, foamy solid. 1H NMR (400 MHz, CDCl3): δ 1.17 (d, J=6.8 Hz, 3H), 1.37 (t, J=7.2 Hz, 3H), 1.37 (t, J=7.2 Hz, 3H), 1.43 (s, 9H), 2.05 (s, 3H), 3.04 (m, 2H), 4.00 (dd, J=12.0, 6.8 Hz, 1H), 4.14 (dd, J=12.0, 3.2 Hz, 1H), 4.32 (q, J=7.2 Hz, 4H), 4.54 (dd, J=12.8, 6.4 Hz, 1H), 5.02 (d, J=8.0 Hz, 1H, NH), 5.12 (m, 1H), 7.05 (dd, J=8.0, 2.0 Hz, 1H), 7.08 (d, J=2.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H). MS (ESI) m/z 564.1 (M+Na)+ and 540.1 (M−H)−.

Workup

  1. additionwas added at 0° C
  2. customThe solution was partitioned between dichloromethane and 10% citric acid
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-400e16f6a40c4051bb207377e95ef1ab
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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