(S)-mandelic acid → HCID 16738474, compound

HRID 2368957Notes

Reaction equation

HRID 2368957 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(=O)[C@H](C1C=CC=CC=1)O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C@H:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 439616(S)-mandelic acidHCID 46193229HCID 46193229, compound

Product 1

HCID 16738474HCID 16738474, compoundYield 49%

Procedure

A sample of 2.0 g (7.3 mmol) of 1-(4′-nitrophenyl)-2-benzylaminopropane (43) was reacted with 1.13 g (7.3 mmol) of (S)-(+)-mandelic acid to give 486 mg (49% based on enantiomeric abundance) of the free amine after workup. 1H NMR (CDCl3) δ□ 1.60 (d, 3H, J=6.3 Hz), 2.73-2.85 (m, 1H), 3.00-3.12 (m, 2H), 3.86 (dd, 2H, J=26 Hz, J=60 Hz), 7.23-7.40 (m, 5H), 7.30 (d, 2H, J=9.0 Hz), 8.14 (d, 2H, J=8.7 Hz); MS (APCI+) m/z (rel): 271 (100); [α]D=−9.3° (c=1.0 MeOH).

Sources & evidence

ORD record
ord-5a401dfacd6e4d44a9a1ad1b820f67f8
Source dataset
uspto-grants-2014_04
Patent number
US08703826B2

Reaction notes

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