Cyclopentanecarbonyl chloride → HCID 57889875, compound

HRID 1820210Notes

Reaction equation

HRID 1820210 reaction equation
Cl.[NH2:2][C@@H:3]([C:18]([N:20]1[CH2:25][CH2:24][C@@:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)([OH:26])[C:22]([CH3:35])([CH3:34])[CH2:21]1)=[O:19])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:36]1([C:41](Cl)=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37]1.CCN(C(C)C)C(C)C>ClCCl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C@@:23]2([OH:26])[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C@H:3]([NH:2][C:41]([CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[O:42])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:21][C:22]2([CH3:35])[CH3:34])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 86614926HCID 86614926, compound

Product 1

HCID 57889875HCID 57889875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl (R)-4-amino-5-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-5-oxopentylcarbamate hydrochloride (50.5 mg, 0.096 mmol) was dissolved in dichloromethane (0.5 mL) and added cyclopentane carbonylchloride (14 μL, 0.12 mmol) followed by DIPEA (42 μL, 0.24 mmol). The solution was stirred for 2 h, concentrated, and partitioned between EtOAc (2 mL) and aq NaHCO3 (0.5 mL). The EtOAc layer was separated, dried over magnesium sulfate, and concentrated to give benzyl (R)-5-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-(cyclopentanecarboxamido)-5-oxopentylcarbamate which was used without further purification.

Workup

  1. concentrationconcentrated
  2. custompartitioned between EtOAc (2 mL) and aq NaHCO3 (0.5 mL)
  3. customThe EtOAc layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b63a9fada6ca41e3af8bd38442c62d75
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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