Methylamine → HCID 18601564, compound

HRID 1589321Notes

Reaction equation

HRID 1589321 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:23]([OH:25])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:27]1[C:31]2C=CC=CC=2N=N1.CN>ClCCl>[CH3:31][NH:27][C:23](=[O:25])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 18601563N-(tert-Butoxycarbonyl)-O-cyclopentyl-L-tyrosine

Product 1

HCID 18601564HCID 18601564, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0°) solution of N-(Tertiarybutoxycarbonyl)-O-cyclopentyl-L-tyrosine (6.89 g, 20 mM) in dichloromethane (40 ml) was added 1-hydroxybenzotriazole (3.32 g, 21 mM) and dicyclohenylcarbodiimide (4.47 g, 21 mM). After 20 minutes at 0° a solution of methylamine (1.34 g, 40 mM) in dichloromethane (20 ml) was added and the reaction mixture was allowed to stir and warm to room temperature overnight. The reaction mixture after filtration and washing with water, dilute (1M) sodium hydroxide, 3N citric acid and water was dried and concentrated in vacuo to an oil. Recrystallisation from ethyl acetate/hexane gave the title compound as white crystals (1 g); m.p. 152°-154°; (Found: C, 66.77; H, 8.47; N, 7.83. C20H30N2O4 requires C, 66.27; H, 8.34; N, 7.73%); δ(CDCl3) 1.40 (9H, s, C(CH3)3); 1.5-2.0 (8H, CH-cyclopentyl); 2.72 (3H, d, J=5 Hz, CONHCH3); 2.95 (2H, m, CH2Tyr); 4.22 (1H, dd, J=7 and 15 Hz,α-CH); 4.72 (1H, br, O--CH (cyclopentyl)); 5.07 (1H, br, CONH); 5.75 (1H, br, CONH); 6.78 (2H, d, J=8 Hz, C6H4); 7.10 (2H, d, J=8 Hz, C6H4).

Workup

  1. filtrationThe reaction mixture after filtration
  2. washwashing with water
  3. additiondilute (1M) sodium hydroxide, 3N citric acid and water
  4. customwas dried
  5. concentrationconcentrated in vacuo to an oil
  6. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d3b0242fc4114520a2e4df2d1de0b47b
Source dataset
uspto-grants-1986_02
Patent number
US04568666

Reaction notes

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