1-O-benzoyl-1,3-propanediol → 3-(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)propyl benzoate

HRID 332706Notes

Reaction equation

HRID 332706 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:35])[NH:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30](O)[CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:17])([CH3:16])[CH3:15].O1CCOC1CC1C=CC(CO)=CC=1.OC1C=C(C=CC=1)C(C1C=CC=CC=1)=O>>[C:1]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:21]([NH:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:35])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 813781-O-benzoyl-1,3-propanediolHCID 830503-HydroxybenzophenoneHCID 71113120tert-Butyl ((3-hydroxyphenyl)(phenyl)methyl)carbamateHCID 86676898(4-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol

Product 1

HCID 710932313-(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)propyl benzoate

Procedure

The title compound was prepared as described in Example 22 Step 3 with 3-hydroxypropyl benzoate (prepared as outlined in Organic & Biomolecular Chemistry, 8(24), 5505-5510; 2010, which is incorporated herein by reference in its entirety) and tert-butyl((3-hydroxyphenyl)(phenyl)methyl)carbamate (derived from the second eluting isomer Chiral Example 1 Step 4) replacing (4-((1,3-dioxolan-2-yl)methyl)phenyl)methanol and 3-hydroxybenzophenone respectively.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-9bfae8273bfd4984901b5a21f3afc130
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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