Methanol → 3-{4-[2-(4-tert-Butoxycarbonylamino-phenyl)-acetoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid

HRID 1628189Notes

Reaction equation

HRID 1628189 reaction equation
C([O:8][C:9](=[O:40])[CH:10]([O:37][CH2:38][CH3:39])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](=[O:35])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:23][CH:22]=2)=[C:14]([CH3:36])[CH:13]=1)C1C=CC=CC=1.CO>CCOC(C)=O>[C:31]([O:30][C:28]([NH:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH:10]([O:37][CH2:38][CH3:39])[C:9]([OH:40])=[O:8])=[CH:13][C:14]=2[CH3:36])=[O:35])=[CH:26][CH:25]=1)=[O:29])([CH3:32])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 887MethanolHCID 668653213-{4-[2-(4-tert-Butoxycarbonylamino-phenyl)-acetoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid benzyl ester

Product 1

HCID 668651483-{4-[2-(4-tert-Butoxycarbonylamino-phenyl)-acetoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-{4-[2-(4-tert-butoxycarbonylamino-phenyl)-acetoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid benzyl ester (0.035 g, 0.064 mmol) in the same manner as described for example 1 with the difference that MeOH was used as the solvent instead of EtOAc. The crude product was purified by column chromatography using DCM/iPrOH (95:5) as the eluent and the title compound was obtained as a solid (0.02 g, 68.4%). 1H NMR (500 MHz, CD3OD): δ 7.40-7.42 (d, 2H), 7.29-7.31 (d, 2H), 7.10-7.15 (m, 2H), 6.86-6.87 (d, 1H), 3.84-3.88 (m, 3H), 3.60-3.62 (m, 1H), 3.26-3.29 (m, 1H), 2.96-3.02 (dd, 1H), 2.80-2.86 (dd, 1H), 1.53 (s, 9H), 1.10-1.13 (t, 3H).

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b3792caa93354d0a8980939b7a6a58a5
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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