Isoamyl Alcohol → HCID 54401291, compound

HRID 2121173Notes

Reaction equation

HRID 2121173 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]2[CH:25]=[CH:24][C:12]([C:13]([NH:15][C@H:16]([C:21]([OH:23])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])=[C:11]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]=2)[CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:44](O)[CH2:45][CH:46]([CH3:48])[CH3:47].[O-]CC.[Na+]>C1COCC1>[CH2:44]([O:22][C:21](=[O:23])[C@H:16]([CH2:17][CH2:18][S:19][CH3:20])[NH:15][C:13](=[O:14])[C:12]1[CH:24]=[CH:25][C:9]([NH:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:10][C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:45][CH:46]([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 31260Isoamyl AlcoholHCID 682631,1'-CarbonyldiimidazoleHCID 2723922Sodium ethoxideHCID 10599017HCID 10599017, compound

Product 1

HCID 54401291HCID 54401291, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(3-pyridylmethylamino)-2-phenylbenzoyl]methionine (200 mg, 0.46 mmol), prepared as in Example 192, carbonyldiimidazole (74 mg, 0.46 mmol), and isoamyl alcohol (40 mg, 0.46 mmol) were combined in 10 mL THF. After 2 hours at room temperature, sodium ethoxide (2.68 M in ethanol, 0.02 mmol) was added. After an additional 18 hours, the mixture was evaporated to dryness, partitioned between ethyl acetate and water, washed with water and brine, dried over Na2SO4, and chromatographed (Ethyl acetate) to give [4-(3-pyridylmethylamino)-2-phenylbenzoyl-L-methionine isoamyl ester (90 mg). MS m/e 506 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 0.90 (d, J=7 Hz, 6H), 1.48 (m, 2H), 1.64 (m, 4H), 1.88 (m, 1H), 2.01 (s, 3H), 2.11 (t, J=7 Hz, 2H), 4.08 (m, 2H), 4.42 (s, 2H), 4.60 (m, 1H), 5.87 (d, J=8 Hz, 1H), 6.51 (d, J=3 Hz, 1H), 6.63 (m, 1H), 7.28-7.44 (m, 5H), 7.68 (m, 2H), 8.55 (m, 1H), 8.63 (s, 1H).

Workup

  1. waitAfter an additional 18 hours
  2. customthe mixture was evaporated to dryness
  3. custompartitioned between ethyl acetate and water
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. customchromatographed (Ethyl acetate)

Sources & evidence

ORD record
ord-0203567931ef42abb293ea936906d84b
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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