1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-benzyl 1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate

HRID 1517844Notes

Reaction equation

HRID 1517844 reaction equation
[OH:1][C@H:2]([CH3:27])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:6](=[O:20])[N:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28]([NH:35][CH2:36][C:37](O)=[O:38])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:31]([O:30][C:28]([NH:35][CH2:36][C:37]([O:1][C@H:2]([CH3:27])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[C:6](=[O:20])[N:5]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:38])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 59383925(R)-benzyl 1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate

Product 1

HCID 86645603(R)-benzyl 1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylateYield 105.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-benzyl 1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (500 mg, 1.36 mmol), Boc-glycine (263 mg, 1.50 mmol), DMAP (17 mg, 0.136 mmol) in dry CH2Cl2 (5 mL) was added EDCI (417 mg, 2.18 mmol). The mixture reaction was stirred for 3 h at rt. TLC analysis showed that the starting material was consumed completely. The organic layer was then washed with water (3 mL×2), aqueous NaH2PO4 (3 mL×2, 2N) and water (3 mL×2). The organic phase was dried over anhydrous Na2SO4, filtrated and concentrated in vacuo to afford the title compound as a thick oil (750 mg).

Workup

  1. customThe mixture reaction
  2. customwas consumed completely
  3. washThe organic layer was then washed with water (3 mL×2), aqueous NaH2PO4 (3 mL×2, 2N) and water (3 mL×2)
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-314be7f3e16b4d9c8099cae668da3631
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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