Dicyclohexylcarbodiimide → HCID 10552575, compound

HRID 1378452Notes

Reaction equation

HRID 1378452 reaction equation
[SH:1][C:2]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH2:11]([O:15][C:16](=[O:35])[C@H:17]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:18][C:19]([C:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:12][CH2:13][CH3:14].ON1C2N=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.C(N(CC)CC)C>[CH2:11]([O:15][C:16](=[O:35])[C@H:17]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:18][C:19]([C:21]1([NH:26][C:7]([C:2]2([SH:1])[CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:9])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 158175841-Sulfanylcyclopentane-1-carboxylic acidHCID 86749398HCID 86749398, compound

Product 1

HCID 10552575HCID 10552575, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 1-mercapto-1-cyclopentanecarboxylic acid (1.74 g, 4.54 mmol) in dichloromethane (50 mL) and triethylamine (0.63 mL) is added [(1-amino-(1-cyclopentyl)carbonyl]-L-tyrosine butyl ester hydrochloride (0.66 g). To this solution is added 1-hydroxy-7-azabenzotriazole (0.68 g, 4.55 mmol) and 1,3-dicyclohexylcarbodiimide (1.03 g, 4.99 mmol). The mixture is stirred for 14 hours and then the solid precipitate is removed by filtration. The organic phase is washed with a saturated solution of sodium bicarbonate (10 mL), brine (10 mL), dried over magnesium sulfate and the solvent is removed to give a clear oil. The oil is purified by flash chromatography (SiO2, hexane/ethyl acetate, 6:4) to give a clear foam. The foam is crystallized from ethyl ether to yield N-[[1-[[(1-mercapto-1-cyclopentyl)carbonyl]amino]-1-cyclopentyl]carbonyl]-L-tyrosine butyl ester, m.p. 106°-107° C.

Workup

  1. customthe solid precipitate is removed by filtration
  2. washThe organic phase is washed with a saturated solution of sodium bicarbonate (10 mL), brine (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is removed
  5. customto give a clear oil
  6. customThe oil is purified by flash chromatography (SiO2, hexane/ethyl acetate, 6:4)
  7. customto give a clear foam
  8. customThe foam is crystallized from ethyl ether

Sources & evidence

ORD record
ord-e5e927817a2744be940cd68c5d7fc6c7
Source dataset
uspto-grants-1997_09
Patent number
US05668158

Reaction notes

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