Sodium Hydroxide → tert-butyl ((1S,4S)-4-(2-mercaptoethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

HRID 1747132Notes

Reaction equation

HRID 1747132 reaction equation
C(=O)([S:3][CH2:4][CH2:5][C@@:6]1([C:19]([N:21]2[CH2:30][CH2:29][C:28]3[N:27]=[CH:26][C:25]([C:31]([F:34])([F:33])[F:32])=[CH:24][C:23]=3[CH2:22]2)=[O:20])[CH2:10][C@H:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]=[CH:7]1)C.[OH-].[Na+]>CO>[SH:3][CH2:4][CH2:5][C@@:6]1([C:19]([N:21]2[CH2:30][CH2:29][C:28]3[N:27]=[CH:26][C:25]([C:31]([F:34])([F:33])[F:32])=[CH:24][C:23]=3[CH2:22]2)=[O:20])[CH2:10][C@H:9]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:8]=[CH:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89856405S-(2-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)ethyl) ethanethioate

Product 1

HCID 86708139tert-butyl ((1S,4S)-4-(2-mercaptoethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step A (1.74 g, 3.39 mmol, 1 eq) in methanol (100 mL) at rt under Ar (degassed) was added 0.2 N NaOH (85 mL, 85 mmol, 5 eq) that was degassed by bubbling Ar through the solution prior to addition. After 2 hr, the methanol was concentrated, 6 N HCl was added until the solution was acidic, the aqueous was extracted with DCM, the organics combined, dried over MgSO4 and concentrated to afford the product of Step B which was used unpurified in the next step. Calculated for C22H28F3N3O3S: 494.2 (M+23). found: 494.1.

Workup

  1. customwas degassed
  2. customby bubbling Ar through the solution
  3. additionto addition
  4. concentrationthe methanol was concentrated
  5. addition6 N HCl was added until the solution
  6. extractionthe aqueous was extracted with DCM
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-82bf0a1621394fc98eb290db127a6811
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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