Lithium Hydroxide → (S)-1-(1-{(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-piperidin-4-yl)-4-methyl-piperazine-2-carboxylic acid

HRID 2267258Notes

Reaction equation

HRID 2267258 reaction equation
[Li+].[OH-].[NH2:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:7]([CH2:14][C@@H:15]([O:36][C:37]([N:39]2[CH2:44][CH2:43][CH:42]([N:45]3[CH2:51][CH2:50][C:49]4[CH:52]=[CH:53][CH:54]=[CH:55][C:48]=4[NH:47][C:46]3=[O:56])[CH2:41][CH2:40]2)=[O:38])[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][C@H:25]3[C:31]([O:33]CC)=[O:32])[CH2:20][CH2:19]2)=[O:17])=[CH:6][C:5]=1[Cl:57]>C1COCC1>[NH2:3][C:4]1[C:9]([C:10]([F:11])([F:13])[F:12])=[CH:8][C:7]([CH2:14][C@@H:15]([O:36][C:37]([N:39]2[CH2:40][CH2:41][CH:42]([N:45]3[CH2:51][CH2:50][C:49]4[CH:52]=[CH:53][CH:54]=[CH:55][C:48]=4[NH:47][C:46]3=[O:56])[CH2:43][CH2:44]2)=[O:38])[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][C@H:25]3[C:31]([OH:33])=[O:32])[CH2:22][CH2:23]2)=[O:17])=[CH:6][C:5]=1[Cl:57]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57807426Ethyl(S)-1-(1-{(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-piperidin-4-yl)-4-methyl-piperazine-2-carboxylate

Product 1

HCID 57807619(S)-1-(1-{(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-piperidin-4-yl)-4-methyl-piperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 mL (1.00 mmol) 2 M LiOH solution were added to 80.0 mg (0.10 mmol) ethyl (S)-1-(1-{(R)-3-(4-amino-3-chloro-5-trifluoromethyl -phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-piperidin-4-yl)-4-methyl-piperazine-2-carboxylate in 1 mL THF and the reaction mixture was stirred for 20 h at RT. This was purified by HPLC without working up; the fractions containing the product were combined and lyophilised.

Workup

  1. customThis was purified by HPLC
  2. additionthe fractions containing the product

Sources & evidence

ORD record
ord-ccced52d86af424cb19b90f6ea407899
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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