Sodium Hydroxide → (1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)cyclopent-2-enecarboxylic acid

HRID 1747118Notes

Reaction equation

HRID 1747118 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708127(1S,4S)-methyl 4-(tert-butoxycarbonylamino)-1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopent-2-enecarboxylate

Product 1

HCID 86708128(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)cyclopent-2-enecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step A (7.89 g, 19.74 mmol, 1 eq) in methanol (100 mL) at rt was added 1 N NaOH (59.2 mL, 59.2 mmol, 3.0 eq). After stirring overnight, the methanol was removed, 1 N HCl was added until the solution was acidic, the solution extracted with DCM, the organics combined, dried over MgSO4, and concentrated to afford the title compound of Step B. 1H NMR (CHLOROFORM-d) δ: 5.85 (br. s., 2H), 4.97 (br. s., 1H), 4.80 (br. s., 1H), 3.71 (br. s., 2H), 1.99-2.41 (m, 3H), 1.92 (br. s., 1H), 1.44 (br. s., 9H), 0.88 (s, 9H), 0.06 (br. s., 6H). ESI-MS (m/z): Calculated for C19H35NO5Si: 408.2 (M+23). found: 408.3.

Workup

  1. customthe methanol was removed
  2. addition1 N HCl was added until the solution
  3. extractionthe solution extracted with DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd229b987ae84d808979daa0558661f5
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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