Hydrochloric Acid → (R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 2267248Notes

Reaction equation

HRID 2267248 reaction equation
[Li+].[OH-].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13](=[O:15])[N:12]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C@@H:25]([C:39]([O:41]CC)=[O:40])[CH2:26][C:27]4[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[C:30]([NH2:37])=[C:29]([Cl:38])[CH:28]=4)=[O:23])[CH2:18][CH2:17]3)[CH2:11][CH2:10][C:9]=2[CH:44]=1.Cl>O.C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13](=[O:15])[N:12]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C@@H:25]([C:39]([OH:41])=[O:40])[CH2:26][C:27]4[CH:32]=[C:31]([C:33]([F:35])([F:36])[F:34])[C:30]([NH2:37])=[C:29]([Cl:38])[CH:28]=4)=[O:23])[CH2:18][CH2:17]3)[CH2:11][CH2:10][C:9]=2[CH:44]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66942197(R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-ethoxycarbonyl-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 66941519(R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.11 g (4.50 mmol) LiOH in 50 mL water was added to a solution of 1.80 g (2.94 mmol) (R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-ethoxycarbonyl-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 50 mL THF and the reaction mixture was stirred for 3 h at RT. The THF was eliminated i. vac., diluted with 100 mL water and acidified with 1 M HCl. The substance precipitated was suction filtered, washed with 50 mL water and dried in the vacuum drying cupboard at 65° C.

Workup

  1. customThe substance precipitated
  2. filtrationfiltered
  3. washwashed with 50 mL water
  4. customdried in the vacuum
  5. customdrying cupboard at 65° C.

Sources & evidence

ORD record
ord-d3d0c06e82104977be045edf9a755761
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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