Methylamine → HCID 59608124, compound

HRID 2384043Notes

Reaction equation

HRID 2384043 reaction equation
C([O:3][C:4](=[O:33])[C@H:5]([CH3:32])[CH2:6][C@H:7]([NH:21][C:22]([C:24]1O[CH:26]=[C:27]([OH:31])[C:28](=[O:30])[CH:29]=1)=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C.[CH3:34][NH2:35]>O>[C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:14][C:9]([CH2:8][C@@H:7]([NH:21][C:22]([C:24]2[N:35]([CH3:34])[CH:26]=[C:27]([OH:31])[C:28](=[O:30])[CH:29]=2)=[O:23])[CH2:6][C@@H:5]([CH3:32])[C:4]([OH:3])=[O:33])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59608212HCID 59608212, compound

Product 1

HCID 59608124HCID 59608124, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of (2R,4S)-5-biphenyl-4-yl-4-[(5-hydroxy-4-oxo-4H-pyran-2-carbonyl)-amino]-2-methyl-pentanoic acid ethyl ester (Example 23-1) (50 mg) in water (1 mL) is added methylamine (1 mL of a 40% solution in water) and the resulting mixture is heated to reflux for 6 hours. The mixture is under reduced pressure and is purified by preparative HPLC using a gradient of 10% MeCN/water to 100% MeCN (0.1% TFA) to elute the title compound; HPLC Retention time 1.21 minutes (condition C): MS 435.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (d, J=7.07 Hz, 3H) 1.45-1.65 (m, 1H) 1.82-1.98 (m, 1H) 2.25-2.38 (m, 1H) 2.63-2.78 (m, 1H) 2.79-2.97 (m, 1H) 4.14-4.32 (m, 1H) 6.45 (br. s., 1H) 7.26-7.39 (m, 2H) 7.45 (t, J=7.58 Hz, 2H) 7.55-7.68 (m, 4H) 8.79 (d, J=9.09 Hz, 1H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. customis purified by preparative HPLC
  4. washto elute the title compound

Sources & evidence

ORD record
ord-79c01c82bf6e497b91947bf2932bc3a5
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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