Water → HCID 67745458, compound

HRID 1735405Notes

Reaction equation

HRID 1735405 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.O.[OH:27][CH:28]([C@@H:38]1[CH2:42][CH2:41][CH2:40][NH:39]1)[CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([N:39]1[CH2:40][CH2:41][CH2:42][C@H:38]1[CH:28]([OH:27])[CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 57152973HCID 57152973, compound

Product 1

HCID 67745458HCID 67745458, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-L-proline (2.93 g), HOBt (4.55 g) and water-soluble carbodiimide hydrochloride (2.88 g) were added to a methylene chloride suspension (30 ml) of (S)-2-[1-hydroxy-2(phenylmethyloxy)ethyl]pyrrolidine (3.00 g) obtained in Example 5a), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was washed with 5% citric acid, saturated sodium hydrogencarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (4.99 g).

Workup

  1. washThe reaction mixture was washed with 5% citric acid, saturated sodium hydrogencarbonate and water in order
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4aa22b85ad034efb8d316ddbd23058a4
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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