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Hydrochloric Acid → (2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acid

HRID 1437575
Notes
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Reaction equation

HRID 1437575 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:4].[OH-].[Na+].Cl>CO>[C:11]([NH:10][C@H:8]1[CH2:7][N:6]([C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1)(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25001500Methyl (2S,4R)-4-benzamido-1-((tert-butoxycarbonyl)glycyl)pyrrolidine-2-carboxylate

Product 1

HCID 16738323(2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
-3 °C

Procedure

To a solution of (2S,4R) methyl-4-benzamido-1-(2-(tert-butoxycarbonyl-amino)acetyl)pyrrolidine-2-carboxylate (23.33 g, 0.0575 mol) in methanol (450 mL) was added NaOH (0.2875 mol, 144 mL of 2N aqueous solution) at −1 to 1° C. over 15 min. The mixture was stirred at −5 to −1° C. for 2.5 h. HCl (0.2875 mol, 144 mL of 2N aqueous solution) was added at −3 to 1° C. over 25 min. MeOH was distilled off under vacuum, then 500 mL of EtOAc was added. The aqueous phase was saturated with NaCl and the phases were separated. The aqueous phase was extracted with 2×250 mL EtOAc and the combined EtOAc solution was dried over MgSO4, and concentrated to afford 22.54 g of (2S,4R) 4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid as a white foamy solid (contains 6.6 wt % EtOAc; 94% yield adjusted to residual EtOAc). 1H NMR (CD3OD, δ, ppm): 7.87-7.79 (m, 2 H), 7.58-7.42 (m, 3 H), 4.81-4.7 (m 1 H), 4.69-4.56 (m, 1 H), 4.05-3.72 (m, 3 H), 3.67-3.49 (m, 1 H), 2.64-2.28 (m, 2 H), 1.43 (s, 9 H). MS (m/z, positive ESI) for M+H: 392; for M+Na: 414.

Workup

  1. distillationMeOH was distilled off under vacuum
  2. addition500 mL of EtOAc was added
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with 2×250 mL EtOAc
  5. dry with materialthe combined EtOAc solution was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b916b9e41a064027b3f0ed16e74de467
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622496B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes