Hydrochloric Acid → HCID 67745442, compound

HRID 1735415Notes

Reaction equation

HRID 1735415 reaction equation
Cl.C(O[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:8])(C)(C)C.[NH:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1C(O)=O.[CH2:30]([N:37]=[C:38]=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.C(N(CC)CC)C>[CH2:19]([O:18][C:16]([CH2:15][CH:14]([C@@H:10]1[CH2:11][CH2:12][CH2:13][N:9]1[C:7]([C@@H:29]1[CH2:28][CH2:27][CH2:23][N:22]1[C:38]([NH:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:39])=[O:8])[OH:21])=[O:17])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 76639Benzyl isocyanateHCID 145742L-ProlineHCID 67745421HCID 67745421, compound

Product 1

HCID 67745442HCID 67745442, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4N Hydrochloric acid (1,4-dioxane solution, 50 ml) was added to (S)-1-(tert-butoxycarbonyl)-2-[2-(ethoxycarbonyl)-1-hydroxyethyl]pyrrolidine (5.73 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue was reacted with N-(benzylamincarbonyl)-L-proline obtained by stirring L-proline (1.15 g), benzyl isocyanate (1.13 g) and triethylamine (1.01 g) in DMF (10 ml), at room temperature for 1 hour, in the same manner as in Example 3-a), to give the title compound (3.36 g).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was reacted with N-(benzylamincarbonyl)-L-proline
  3. customobtained
  4. waitat room temperature for 1 hour

Sources & evidence

ORD record
ord-3b9c64c6aff64c229ef36f02576ec0e0
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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