Triethylamine → (S)-Methyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylate

HRID 1471295Notes

Reaction equation

HRID 1471295 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[CH3:38][O:39][C:40](=[O:46])[C@@H:41]1[CH2:45][CH2:44][CH2:43][NH:42]1>CN(C=O)C.ClCCl>[CH3:38][O:39][C:40](=[O:46])[C@@H:41]1[CH2:45][CH2:44][CH2:43][N:42]1[C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 726987N-Carbobenzoxy-L-valine2×HCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 14032133(S)-Methyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Cbz-valine (2.5 g, 10 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.6 g, 11 mmol) and triethylamine (2.0 g, 20 mmol) in DMF (10 mL) is added dropwise a solution of proline methyl ester hydrochloride (1.8 g, 11 mmol) in DMF (5 mL). The solution is stirred at room temperature and the reaction monitored by TLC until the disappearance of N-Cbz-valine. The reaction solution is then diluted with dichloromethane (30 mL) and the organic layer is extracted with 0.1 N HCl (20 mL), water (20 mL), then dried over Na2SO4. The solvent is removed in vacuo to afford the desired compound.

Workup

  1. extractionthe organic layer is extracted with 0.1 N HCl (20 mL), water (20 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-974f3656bbd14ffda6cf5283d4695c19
Source dataset
uspto-grants-2015_04
Patent number
US09011918B2

Reaction notes

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