Lithium Hydroxide → HCID 67301308, compound

HRID 643615Notes

Reaction equation

HRID 643615 reaction equation
[Li+].[OH-].[O:3]=[C:4]1[N:10]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C@@H:20]([C:31]([O:33]C)=[O:32])[CH2:21][C:22]3[CH:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[C:24]([CH3:30])[CH:23]=3)=[O:18])[CH2:13][CH2:12]2)[CH2:9][CH2:8][C:7]2[CH:35]=[CH:36][CH:37]=[CH:38][C:6]=2[NH:5]1>O.C1COCC1>[O:3]=[C:4]1[N:10]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C@@H:20]([C:31]([OH:33])=[O:32])[CH2:21][C:22]3[CH:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[C:24]([CH3:30])[CH:23]=3)=[O:18])[CH2:13][CH2:12]2)[CH2:9][CH2:8][C:7]2[CH:35]=[CH:36][CH:37]=[CH:38][C:6]=2[NH:5]1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 67302062HCID 67302062, compound

Product 1

HCID 67301308HCID 67301308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 500 mg (20.9 mmol) LiOH in 10 mL water was added to a solution of 6.7 g (13.6 mmol) of (R)-2-(4-amino-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(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 overnight at RT. To complete the reaction another 300 mg (12.5 mmol) LiOH were added and the reaction solution was stirred for 3 h at 40° C. It was evaporated down i.vac., the residue was taken up in 15% K2CO3 solution and extracted exhaustively with DCM. The aqueous phase was acidified with 4 M HCl, exhaustively extracted with DCM and the combined organic phases were dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was reacted further without purification.

Workup

  1. additionwere added
  2. stirringthe reaction solution was stirred for 3 h at 40° C
  3. customIt was evaporated down i.vac
  4. extractionextracted exhaustively with DCM
  5. extractionexhaustively extracted with DCM
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customwas reacted further without purification

Sources & evidence

ORD record
ord-ab2da706d70e479daeeea0b5178b1934
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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