Lithium Hydroxide → HCID 89930856, compound

HRID 527738Notes

Reaction equation

HRID 527738 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:57])[C@@H:9]([CH3:56])[C:10]([NH:12][C@H:13]([C:34]([N:36]1[C@H:40]([C:41](=[O:53])[NH:42][C@H:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH2:46][CH2:45][CH2:44]2)[CH2:39][Si:38]([CH3:55])([CH3:54])[CH2:37]1)=[O:35])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)=[O:23])=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO.O>[C:1]([O:5][C:6]([N:8]([CH3:57])[C@@H:9]([CH3:56])[C:10]([NH:12][C@H:13]([C:34]([N:36]1[C@H:40]([C:41](=[O:53])[NH:42][C@H:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH2:46][CH2:45][CH2:44]2)[CH2:39][Si:38]([CH3:54])([CH3:55])[CH2:37]1)=[O:35])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)=[O:23])=[CH:19][CH:20]=1)=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89930824HCID 89930824, compound

Product 1

HCID 89930856HCID 89930856, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-((4-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)phenyl)carbamoyl)benzoate (160 mg, 0.200 mmol) and LiOH (300 mg) in MeOH (6 mL) and H2O (2 mL) was stirred at rt for 2.5 h. Most of the MeOH was removed in vacuo and the residue was mixed with EtOAc and 1N HCl (60 mL). The organic layer was separated, dried over MgSO4 and concentrated in vacuo to obtain the title compound (140 mg, 0.179 mmol, 71% yield) as a white solid. MS(ESI+) m/z 784.4 (M+H)+.

Workup

  1. customMost of the MeOH was removed in vacuo
  2. additionthe residue was mixed with EtOAc and 1N HCl (60 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a0d969438ab4cd3b460d104c9767183
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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