(R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid → (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide

HRID 1830198Notes

Reaction equation

HRID 1830198 reaction equation
[CH:1]1([CH2:7][C@H:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:21][CH:22]([CH2:36][CH3:37])[C@@H:23]([C:25]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=1)[OH:24]>>[CH:1]1([CH2:7][C@H:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([NH:21][C@H:22]([C:23]([C:25]2[N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:27][N:26]=2)=[O:24])[CH2:36][CH3:37])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 59972959(R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acidHCID 67301524(S)-2-Amino-1-(5-phenyl-1,2,4-oxadiazol-3-yl)-butan-1-ol

Product 1

HCID 58649537(R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide

Procedure

Similarly prepared according to the general procedure given for Example 43 but using (R)-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid, prepared as described in reference 21, and (S)-2-amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol, prepared as in reference 26; MS: 519 (M+Na), LC-MS retention time 4.5 min; 1H NMR (CDCl3) 8.19 (d, J=7 Hz, 2H), 7.65–7.51 (m. 3H), 6.64 (d, J=7 Hz, 1H), 5.44–5.38 (m, 1H), 3.69–3.38 (m, 8H), 3.05–2.98 (m, 1H), 2.76 (dd, J=16 Hz & 10 Hz, 1H), 2.26 (dd, J=16 Hz & 3 Hz, 1H), 2.10 (m, 1H), 1.80 (m, 1H), 1.75–1.59 (m, 6H), 1.28–1.13 (m, 5H), 1.03–0.98 (t, J=7 Hz, 3H), 0.92–0.81 (m, 2H).

Workup

  1. customSimilarly prepared
  2. customprepared

Sources & evidence

ORD record
ord-4b5b3611c79646f98e7f66e342c54b6d
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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