Ethyl chloroformate → HCID 59656343, compound

HRID 1726503Notes

Reaction equation

HRID 1726503 reaction equation
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([NH:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]([OH:27])[CH3:26])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1.C(=O)([O-])[O-].Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CO>[CH2:36]([O:35][C:33]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]([OH:27])[CH3:26])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH2:10]1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 19660Carbonate IonHCID 66998005HCID 66998005, compound

Product 1

HCID 59656343HCID 59656343, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(1-hydroxy-ethyl)-naphthalene-1-sulfonic acid piperidin-4-ylamide acetic acid salt 37 (290 mg, 0.74 mmol) in MeOH (10 mL) was added MP-Carbonate (1.45 g, 3.69 mmol, 2.54 mmol/g). After shaking at 25° C. for lh, the solution was filtered. To the resultant solution was added ethyl chloroformate (120 mg, 1.11 mmol). After stirred for another 2 h at 25° C., the solution was concentrated in vacuo to give a solid. The crude material was purified by Flash column chromatography (CH2Cl2: MeOH) to provide 4-[4-(1-hydroxy-ethyl)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester 38. LC/MS showed m/z 407 (M+H)+.

Workup

  1. filtrationthe solution was filtered
  2. stirringAfter stirred for another 2 h at 25° C.
  3. concentrationthe solution was concentrated in vacuo
  4. customto give a solid
  5. customThe crude material was purified by Flash column chromatography (CH2Cl2: MeOH)

Sources & evidence

ORD record
ord-a61859d8e8444ee287a9d5f596fb44bc
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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