Acetic Anhydride → HCID 57733336, compound

HRID 1962408Notes

Reaction equation

HRID 1962408 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=O)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([C:13]1[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:17])[O:18][C:11]=1[NH:10][C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH3:9])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 577332512-[2-Oxo-2-[[(1S)-1-phenylpropyl]amino]ethyl]benzoic acid

Product 1

HCID 57733336HCID 57733336, compound

Procedure

A mixture of 2-[((S)-1-phenyl-propylcarbamoyl)-methyl]-benzoic acid (10 g), acetic anhydride (50 ml), and N,N-dimethylaminopyridine (100 mg) was heated at gentle reflux (Tmax=+124° C.) for 7 min and evaporated in vacuo at +50° C. to give the title compound as a yellow-brown solid (11.1 g, purity 98% by NMR). LC-MS (m/z) 322.3 (MH+); tR=1.72. 1H NMR (500 MHz, DMSO-d6): 0.89 (t, J=7.2 Hz, 3H), 1.86-1.97 (m, 2H), 2.56 (s, 3H), 4.95 (q, J=7.1 Hz, 1H, CH—NH), 7.26 (t, J=7.5 Hz, 1H), 7.29 (unres. m, 1H), 7.36-7.41 (unres m., 3H), 7.71 (t, J=7.5 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 7.98 (d, J=7.8 Hz, 1H), 11.53 (d, J=7.6 Hz, 1H, NH). 13C APT NMR (125 MHz, DMSO-d6, δ(DMSO-d6)=39.87 ppm): 10.68 (CH3), 30.0 (CH2), 31.57 (CH3), 57.01 (CH), 92.44 (C), 114.88 (C), 124.2 (CH), (CH), 124.26 (CH), 126.65 (CH), 127.8 (CH), 129.05 (CH), 129.93 (CH), 135.71 (CH), 138.68 (C), 141.86 (C), 158.51 (C), 160.55 (C), 194.82 (C, MeCO).

Workup

  1. temperaturewas heated
  2. temperatureat gentle reflux (Tmax=+124° C.) for 7 min
  3. customevaporated in vacuo at +50° C.

Sources & evidence

ORD record
ord-fac8eb0dd96d43f2a010e436443b9735
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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