Hydrochloric Acid → (3R*,5S*)-3-Amino-5-[(2-chloro-benzyl)-cyclopropyl-carbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

HRID 1698303Notes

Reaction equation

HRID 1698303 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@@H:22]([C:24](=[O:37])[N:25]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])[CH:26]4[CH2:28][CH2:27]4)[CH2:21][C@@H:20]([NH:38]C(OC(C)(C)C)=O)[CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl>>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C@@H:22]([C:24](=[O:37])[N:25]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])[CH:26]4[CH2:27][CH2:28]4)[CH2:21][C@@H:20]([NH2:38])[CH2:19]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69067630(3R*,5S*)-3-tert-Butoxycarbonylamino-5-[(2-chloro-benzyl)-cyclopropylcarbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 69071033(3R*,5S*)-3-Amino-5-[(2-chloro-benzyl)-cyclopropyl-carbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Procedure

A mixture of (3R*,5S*)-3-tert-butoxycarbonylamino-5-[(2-chloro-benzyl)-cyclopropylcarbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (186 mg, 0.295 mmol) and HCl (5M in 2-propanol, 2 mL, 10 mmol) is stirred for 2 h at RT. The mixture is evaporated and the residue dried to afford the title compound as a beige amorphous solid. MS: 530.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 6.02 min.

Workup

  1. customThe mixture is evaporated
  2. customthe residue dried

Sources & evidence

ORD record
ord-45865457c62e41bfa62c82dc1a86e6f4
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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