Hydrochloric Acid → HCID 89930810, compound

HRID 527755Notes

Reaction equation

HRID 527755 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:54])[C@@H:9]([CH3:53])[C:10]([NH:12][C@H:13]([C:31]([N:33]1[C@H:37]([C:38](=[O:50])[NH:39][C@H:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:43][CH2:42][CH2:41]2)[CH2:36][Si:35]([CH3:52])([CH3:51])[CH2:34]1)=[O:32])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]([CH3:54])[C@@H:9]([CH3:53])[C:10]([NH:12][C@H:13]([C:31]([N:33]1[C@H:37]([C:38](=[O:50])[NH:39][C@H:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:43][CH2:42][CH2:41]2)[CH2:36][Si:35]([CH3:51])([CH3:52])[CH2:34]1)=[O:32])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89930883HCID 89930883, compound

Product 1

HCID 89930810HCID 89930810, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 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)-[1,1′-biphenyl]-4-carboxylate (40 mg, 0.053 mmol) in THF (1 mL) and MeOH (0.5 mL) was added LiOH solution (0.48 mL, 0.95 mmol). The resulting mixture was stirred at rt overnight and acidified (1N HCl) to pH 1. The resulting mixture was extracted with ethyl acetate (2×). The organic layer was separated, dried over MgSO4 and concentrated in vacuo to give the title compound. MS(ESI+) m/z 741.5 (M+H)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-788e086361064576a13e6b8ad1050360
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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