Hydrochloric Acid → HCID 17939473, compound

HRID 2416730Notes

Reaction equation

HRID 2416730 reaction equation
[O:1]=[C:2]1[CH:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][N:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)C(OC(C)(C)C)=O)=[CH:16][C:5]=2[CH2:4][N:3]1[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1.Cl>O1CCOCC1>[O:1]=[C:2]1[CH:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[CH:16][C:5]=2[CH2:4][N:3]1[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22632202HCID 22632202, compound

Product 1

HCID 17939473HCID 17939473, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(±)-3-Oxo-8-[3-[N-(pyridin-2-yl)-N-(tert-butoxycarbonyl)amino]-1-propyloxy]-2-(4-trifluoromethylbenzyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic acid (0.158 g, 0.25 mmol) was treated with 4 M HCl in dioxane (3 mL) at RT for 1 h, then the solution was concentrated. ODS chromatography (gradient 5-60% CH3CN/H2O containing 0.1% TFA over 1 h), concentration and lyophilization gave the title compound (0.117 g, 82%): MS (ES) m/e 528.4 (M+H)+. Anal. Calcd for C28H28N3O4.1 CF3CO2H.1.5 H2O: C, 53.89; H, 4.82; N. 6.28. Found: C, 53.55; H, 4.55; N, 6.04.

Workup

  1. concentrationthe solution was concentrated
  2. concentrationODS chromatography (gradient 5-60% CH3CN/H2O containing 0.1% TFA over 1 h), concentration and lyophilization

Sources & evidence

ORD record
ord-0c93c3609e664e19844412c86475a0ce
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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