Triethylamine → HCID 86621602, compound

HRID 1171246Notes

Reaction equation

HRID 1171246 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:11]([O:13][C@H:14]([CH3:21])[C@H:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].C(N(CC)CC)C.[C:43]([O:46][CH2:47][CH3:48])(=[O:45])C>ClCCl.CCCCCC>[CH2:34]([O:33][C:31]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:11]([O:13][C@H:14]([CH3:21])[C@H:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][C:43]([O:46][CH2:47][CH3:48])=[O:45])=[O:32])[CH3:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 86621601HCID 86621601, compound

Product 1

HCID 86621602HCID 86621602, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (1R,2R)-2-acetyloxy-1-methylpropyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (34) (0.5 g, 1.2 mmol) and ethyl chloroformate (0.3 mL, 3.0 mmol) in anhydrous dichloromethane, triethylamine (0.4 mL, 3.0 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 (25% ethyl acetate in hexane) provided the title compound (35) (0.6 g, 90% yield) as a white, foamy solid. 1H NMR (400 MHz, CDCl3): δ 1.11 (d, J=6.4 Hz, 3H), 1.13 (d, J=6.4 Hz, 3H), 1.34 (t, J=7.2 Hz, 3H), 1.35 (t, J=7.2 Hz, 3H), 1.40 (s, 9H), 2.02 (s, 3H), 3.02 (dd, J=14.0, 6.8 Hz, 1H), 3.07 (dd, J=14.0, 6.8 Hz, 1H), 4.27 (q, H=7.2 Hz, 2H), 4.28 (q, J=7.2 Hz, 2H), 4.51 (dd, J=14.0, 6.8 Hz, 1H), 4.93 (m, 2H), 5.03 (d, J=8.4 Hz, 1H, NH), 7.03 (dd, J=8.0, 2.0 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 7.16 (d, J=8.0 Hz, 1H). MS (ESI) m/z 578.1 (M+Na)+.

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-e949f5bf536d4da3b412399cc47198d5
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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