Triethylamine → HCID 10530305, compound

HRID 1720351Notes

Reaction equation

HRID 1720351 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C@H:5]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[NH:6][C:7]([C:9]1([NH:14][C:15](=[O:21])[C@@H:16]([SH:20])[CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8])[CH3:2].[CH:31]1([C:36](O)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:30])[C@H:5]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[NH:6][C:7]([C:9]1([NH:14][C:15](=[O:21])[C@@H:16]([S:20][C:36]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:37])[CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 181649HOAtHCID 10646596HCID 10646596, compound

Product 1

HCID 10530305HCID 10530305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[[1-[(2-(S)-mercapto-3-methyl-1-oxobutyl)amino]-1-cyclopentyl]-carbonyl]-L-tyrosine ethyl ester (0.32 g, 0.73 mmole), cyclopentanecarboxylic acid (0.083 g, 0.73 mmole), dicyclohexylcarbodiimide (0.15 g, 0.73 mmole), 1-hydroxy-7-azabenzotriazole (0.10 g, 0.73 mmole), and triethylamine (0.10 ml, 0.73 mmole) in methylene chloride (30 ml) is stirred overnight at room temperature. The resulting mixture is filtered, washed with sodium bicarbonate solution, then with brine, dried over magnesium sulfate and evaporated to dryness. The residue is purified by flash chromatography on silica gel eluting with hexane ethyl acetate. The pure fractions are concentrated and the residue is crystallized from diethyl ether to yield N-[[1-[(2-(S)-cyclopentylcarbonylmercapto-3-methyl- 1-oxobutyl)amino]-1-cyclopentyl]-carbonyl]-L-tyrosine ethyl ester, m.p. 130°-131° C., the compound of formula Ill wherein R4 is 4-hydroxyphenyl, R2 is ethyl, R3 is cyclopentylcarbonyl, and R4 is isopropyl.

Workup

  1. filtrationThe resulting mixture is filtered
  2. washwashed with sodium bicarbonate solution
  3. dry with materialwith brine, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is purified by flash chromatography on silica gel eluting with hexane ethyl acetate
  6. concentrationThe pure fractions are concentrated
  7. customthe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-9c4ab6268e8f448486a7ba0fc9f407ea
Source dataset
uspto-grants-1996_04
Patent number
US05506244

Reaction notes

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