Diisopropylethylamine → (2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester

HRID 643822Notes

Reaction equation

HRID 643822 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:34]([O:36][C:37]([C@@:39]1([NH2:44])[CH2:41][C@H:40]1[CH:42]=[CH2:43])=[O:38])[CH3:35].[C:45]([N:52]1[CH2:60][C@H:58]([OH:59])[CH2:57][C@H:53]1[C:54](O)=[O:55])([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]>ClCCl>[C:48]([O:47][C:45]([N:52]1[CH2:60][C@H:58]([OH:59])[CH2:57][C@H:53]1[C:54](=[O:55])[NH:44][C@@:39]1([C:37]([O:36][CH2:34][CH3:35])=[O:38])[CH2:41][C@@H:40]1[CH:42]=[CH2:43])=[O:46])([CH3:51])([CH3:50])[CH3:49]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10820795rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

Product 1

HCID 57563804(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of HATU (6 g), diisopropylethylamine (6.8 mL), (1R,2S)-1-amino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (1.5 g) and BOC-L-hydroxyproline (1.6 g) in dichloromethane was stirred for 1 hrs. The mixture was extracted with DCM-NaHCO3 (aq) dried and concentrated. HPLC purity ca 90% M+H+ 369.1.

Workup

  1. extractionThe mixture was extracted with DCM-NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a917d2c4992542d2a13a220ab8f55a20
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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