Citric Acid → HCID 67745436, compound

HRID 1735402Notes

Reaction equation

HRID 1735402 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[OH:18][CH:19]([C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]1)[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:34]([NH:41][C:42]([N:44]1[CH2:51][CH2:50][CH2:49][C@H:45]1[C:46](O)=[O:47])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N1CCC[C@H]1C(O)=O.C(N=C=O)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(N(CC)CC)C>[OH:18][CH:19]([C@@H:29]1[CH2:33][CH2:32][CH2:31][N:30]1[C:46]([C@@H:45]1[CH2:49][CH2:50][CH2:51][N:44]1[C:42]([NH:41][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:43])=[O:47])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 6

HCID 311Citric AcidHCID 76639Benzyl isocyanateHCID 145742L-ProlineHCID 199401P,P-Diphenylphosphinic azideHCID 15389022HCID 15389022, compoundHCID 57152973HCID 57152973, compound

Product 1

HCID 67745436HCID 67745436, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

Diphenylphosphoryl azide (259.2 g), triethylamine (80.8 g) and (S)-2-[1-hydroxy-2-(phenylmethyloxy)ethyl]pyrrolidine (176.6 g) were added to a solution of N-(benzylaminocarbonyl)-L-proline obtained by stirring L-proline (91.9 g), benzyl isocyanate (90.3 g) and triethylamine (80.8 g) in DMF (900 ml) at room temperature for 1 hour, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a 7% aqueous solution of citric acid and extracted with ethyl acetate. The extract was washed with water, saturated sodium hydrogenbicarbonate and water in order, dried over sodium sulfate, and concentrated to give the title compound (330.9 g).

Workup

  1. customobtained
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, saturated sodium hydrogenbicarbonate and water in order
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8b0bb9671449e1b506cf70dbf27d8b
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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