Triethylamine → HCID 10530305, compound

HRID 1378455Notes

Reaction equation

HRID 1378455 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 (0.083g, 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 III 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-83a20551946744fd8c844f1f15310942
Source dataset
uspto-grants-1997_09
Patent number
US05668158

Reaction notes

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