Ammonia → (R,R)-N-[5-[1-Hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]formamide

HRID 572704Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:5]([OH:26])[CH2:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.C1C[O:41][CH2:40]C1.C(OC=O)(=O)C.N>C1(C)C=CC=CC=1>[CH2:31]([O:30][C:29]1[CH:28]=[CH:27][C:4]([CH:5]([OH:26])[CH2:6][N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]([CH3:18])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[CH:3][C:2]=1[NH:1][CH:40]=[O:41])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 15 °C

Procedure

3-amino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)aminomethyl]benzyl alcohol (100 gms, 0.2 M), toluene 0.2 lit and 0.2 lit THF, were charged in a reactor. The reaction mass was cooled to 15° C. and 35 ml of 3:2 formic acid-acetic anhydride was introduced maintaining temperature below 20° C. The reaction mass was further stirred at 20-30° C. for 1 hour and concentrated under reduced pressure. The residue obtained was dissolved in toluene (0.65 lit) and basified with liquor ammonia. The organic layer was separated, washed with water and concentrated under reduced pressure below 35° C. to yield the title compound. (100 gms, 94.66%)

Workup

additionwere charged in a reactor
temperaturemaintaining temperature below 20° C
concentrationconcentrated under reduced pressure
customThe residue obtained
customThe organic layer was separated
washwashed with water
concentrationconcentrated under reduced pressure below 35° C.

Sources & evidence

ORD record: ord-e56bb5d09cad452faad9466d50efa315
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029421B2

Reaction notes

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