Cyclohexylamine → 1-[[[(S)-3-[[(Cyclohexylamino)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline

HRID 620040Notes

Reaction equation

HRID 620040 reaction equation
C1(N)CCCCC1.[N+](C1C=CC(OC(N[C@@H](CC2C=CC=CC=2)C(=O)CN(C)C(N2CCC[C@H]2C(OCC2C=CC=CC=2)=O)=O)=O)=CC=1)([O-])=O.[CH:51]1([NH:57][C:58]([NH:60][C@@H:61]([CH2:84][C:85]2[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=2)[C:62](=[O:83])[CH2:63][N:64]([CH3:82])[C:65]([N:67]2[CH2:81][CH2:80][CH2:79][C@H:68]2[C:69]([O:71]CC2C=CC=CC=2)=[O:70])=[O:66])=[O:59])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1>C1(C)C=CC=CC=1>[CH:51]1([NH:57][C:58]([NH:60][C@@H:61]([CH2:84][C:85]2[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=2)[C:62](=[O:83])[CH2:63][N:64]([CH3:82])[C:65]([N:67]2[CH2:81][CH2:80][CH2:79][C@H:68]2[C:69]([OH:71])=[O:70])=[O:66])=[O:59])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 141272261-[[[(S)-3-[[(4-nitrophenoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl esterHCID 1317159141-[[[(S)-3-[[(cyclohexylamino)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester

Product 1

HCID 141272401-[[[(S)-3-[[(Cyclohexylamino)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Cyclohexylamine (1 ml., 8.7 ml., 8.7 mmole) is added to a cold (0°) solution of 1-[[[(S)-3-[[(4-nitrophenoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (0.9 g., 1.58 mmole) in toluene in one portion. The solution turns yellow immediately and TLC indicates all starting material has been consumed. The resulting solution is washed sequentially with water, 1N hydrochloric acid, and 10% sodium bicarbonate. The organic layer is dried (MgSO4) and concentrated to a pale yellow oil. The crude product is purified (2x) by preparative layer chromatography using ethyl acetate as eluant to give 0.31 g. of 1-[[[(S)-3-[[(cyclohexylamino)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester as a clear, colorless salt.

Workup

  1. customhas been consumed
  2. washThe resulting solution is washed sequentially with water, 1N hydrochloric acid, and 10% sodium bicarbonate
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated to a pale yellow oil
  5. customThe crude product is purified (2x) by preparative layer chromatography
  6. customto give 0.31 g

Sources & evidence

ORD record
ord-7a8dc6b29eb44743bcf202635d2c3933
Source dataset
uspto-grants-1989_04
Patent number
US04818757

Reaction notes

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