Acetyl chloride → HCID 54043249, compound

HRID 2230235Notes

Reaction equation

HRID 2230235 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:7][C:8](=[O:39])[CH:9]([NH:23][C:24]([C:26]1([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)=[CH:13][CH:12]=1)[CH3:6].CCN(CC)CC>C(Cl)Cl>[CH2:5]([O:7][C:8](=[O:39])[CH:9]([NH:23][C:24]([C:26]1([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27][CH2:28][CH2:29][CH2:30]1)=[O:25])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:1](=[O:3])[CH3:2])[CH2:18]2)=[CH:15][CH:16]=1)[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54303891HCID 54303891, compound

Product 1

HCID 54043249HCID 54043249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (50 mL, 0.70 mmol) is added slowly to a solution of 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-[4-(piperidin-3-yl)-phenyl]-propionic acid ethyl ester (277 mg, 0.57 mmol) and 11 mL (0.79 mmol) of Et3N in 2 mL of CH2Cl2. The reaction mixture is stirred at 0° C. for 2 h, and then partitioned between saturated aqueous NaHCO3 solution and CH2Cl2. The organic phase is washed with brine, dried over MgSO4, filtered, and concentrated. The residue is purified by chromatography on silica gel (EtOAc) to furnish 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-[4-(1-acetyl-piperidin-3-yl)-phenyl]-propionic acid ethyl ester; 1H NMR (300 MHz, CDCl3) δ7.00-7.15 (m, 4 H), 4.80-4.90 (m, 1 H), 4.70 (br t, 2 H), 4.15 (q, 2 H), 3.00-3.15 (m, 3 H), 2.45-2.70 (m, 2 H), 2.12, 2.08 (s each, 3 H) 1.95-2.40 (m, 6 H), 1.50-1.95 (m, 8 H), 1.40 (s, 9 H), 1.20 (t, 3 H).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 solution and CH2Cl2
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-2e8152a517bf475f828821eaa951b2ac
Source dataset
uspto-grants-2002_07
Patent number
US06423727B1

Reaction notes

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