Lithium Hydroxide → HCID 68676918, compound

HRID 491138Notes

Reaction equation

HRID 491138 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([OH:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:11][C:10]=1[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([N:30]2[CH2:36][CH2:35][C:34]3[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=3[NH:32][C:31]2=[O:41])[CH2:26][CH2:25]1.[Li+].[OH-].C1C[O:47][CH2:46]C1>O>[O:41]=[C:31]1[N:30]([CH:27]2[CH2:26][CH2:25][N:24]([C:46]([O:22][C@@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][C:12]3[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:10]([Cl:23])[CH:11]=3)=[O:47])[CH2:29][CH2:28]2)[CH2:36][CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=2[NH:32]1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 66942108HCID 66942108, compound

Product 1

HCID 68676918HCID 68676918, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(R)-2-(4-benzyloxy-3-chloro-5-methyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate was prepared analogously to Example 7f from 7.0 g (20.9 mmol) methyl(R)-3-(4-benzyloxy-3-chloro-5-methyl-phenyl)-2-hydroxy-propionate and 5.2 g (21.2 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one. The crude product was dissolved in 150 mL THF and combined with a solution of 0.50 g (20.6 mmol) LiOH in 50 mL water. The reaction mixture was stirred overnight at RT, combined with water and the organic solvent was eliminated i.vac. The aqueous phase was washed twice with EtOAc and acidified with 21 mL 1 M HCl. The resulting oil was exhaustively extracted with EtOAc. The combined organic extracts were dried, filtered and evaporated down i.vac.

Workup

  1. washThe aqueous phase was washed twice with EtOAc
  2. extractionThe resulting oil was exhaustively extracted with EtOAc
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. customevaporated down i.vac

Sources & evidence

ORD record
ord-fb628bdeaafc44af9c35a72d78a49ddb
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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