Triethylamine → HCID 57506714, compound

HRID 2071109Notes

Reaction equation

HRID 2071109 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].CCN(CC)CC.[C:17]([N:27]1[CH2:34][CH2:33][CH2:32][C@@H:28]1[C:29](O)=[O:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[OH:8][CH2:7][C@H:5]([NH:6][C:29]([C@H:28]1[CH2:32][CH2:33][CH2:34][N:27]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:30])[C:4]([O:3][CH3:2])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 57506714HCID 57506714, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-Serine methyl ester hydrochloride (Aldrich, 5.0 g, 32.0 mmoles), in CH2Cl2 (150 mL) at 0° C., were added Et3N (4.88 mL, 35.2 mmoles), Cbz-D-Proline (8.01 g, 32.0 mmoles) and DCC (7.26 g, 35.2 mmoles) sequentially. The reaction was allowed to warm to room temperature and stirred overnight. All the solvent was evaporated and the residue was triturated with ethyl acetate and the precipitate was filtered off. The filtrate was concentrated under low pressure and chromatographed on silica gel (70% ethyl acetate/30% chloroform) to yield 8.5 g of (R)-benzyl 2-((S)-3-hydroxy-1-methoxy-1-oxopropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate.

Workup

  1. customAll the solvent was evaporated
  2. customthe residue was triturated with ethyl acetate
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated under low pressure
  5. customchromatographed on silica gel (70% ethyl acetate/30% chloroform)

Sources & evidence

ORD record
ord-87eb5a36ace04dbd9397b90e84a960e2
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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