Ethyl Acetate → HCID 68767051, compound

HRID 1170410Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:31])[C@@:11]([NH2:30])([CH3:29])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[C:16]([NH:21][C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:15]=1.CCOC(C)=O.C([O-])(O)=O.[Na+].C(Cl)Cl.CO>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10](=[O:31])[C@@:11]([NH2:30])([CH3:29])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]2[O:28][C:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N:21][C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A suspension of (R)-2-Amino-4-(3-hexanoylamino-4-hydroxy-phenyl)-2-methyl-butyric acid methyl ester trifluoro acetic acid salt (460 mg, 1.02 mmol) in dry toluene was heated under pressure (microwave Emrys optimizer) to 200° C. for 10 minutes. After cooling to RT the reaction mixture was distributed between AcOEt and a saturated aqueous NaHCO3 solution. Silica gel chromatography (eluent CH2Cl2/MeOH 10/1) provided the title compound as an amorphous colorless solid. 1H-NMR (DMSO-d6): 7.51 (d, J=8.3 Hz; 1H), 7.42 (d, J=1.2 Hz; 1H), 7.12 (dd, J=8.3, 1.2 Hz; 1H), 3.60 (s; 3H), 2.88 (t, J=7.4 Hz; 2H), 2.71-2.63/2.58-2.50 (m; 2H), 1.92 (bs; 2H), 1.90-1.82/1.80-1.73 (m; 2H), 1.43-1.28 (m; 4H), 1.22 (s; 3H), 0.85 (m; 3H).

Workup

temperatureAfter cooling to RT the reaction mixture

Sources & evidence

ORD record: ord-887dd4f6c4e24ce4958a6d02cce68464
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825260B2

Reaction notes

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