Hydrochloric Acid → (S)-3-(m-tolyloxy)-2-(tritylamino)propanoic acid

HRID 625883Notes

Reaction equation

HRID 625883 reaction equation
[C:1]1([CH3:34])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C@H:9]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12]C)=[O:11])[CH:2]=1.[OH-].[Li+].O.Cl>CO.C1COCC1.CCOC(C)=O>[C:1]1([CH3:34])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C@H:9]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])[CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 90457174(S)-methyl 3-(m-tolyloxy)-2-(tritylamino)propanoate

Product 1

HCID 90456374(S)-3-(m-tolyloxy)-2-(tritylamino)propanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask equipped with a stir bar and charged with (S)-methyl 3-(m-tolyloxy)-2-(tritylamino)propanoate (8.28 g, 18.34 mmol) in MeOH (30 mL) and THF (30 mL) was added lithium hydroxide in water (55.0 mmol, 27.5 mL). The mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with aq. 2N HCl. The mixture was diluted with EtOAc and the organic phase was isolated and washed with brine; dried over MgSO4; filtered; then concentrated in vacuo. The resulting residue was purified via silica gel chromatography to afford (S)-3-(m-tolyloxy)-2-(tritylamino)propanoic acid, 1.47 g (18%). 1H-NMR (400 MHz, CDCl3) δ 7.44 (d, J=7.1 Hz, 6H), 7.35-7.24 (m, 8H), 7.09 (t, J=7.8 Hz, 1H), 6.76 (d, J=7.6 Hz, 1H), 6.52 (s, 1H), 6.46 (d, J=8.1 Hz, 1H), 4.07 (dd, J=9.2, 2.3 Hz, 1H), 3.71 (t, J=3.2 Hz, 1H), 2.79 (dd, J=9.2, 4.0 Hz, 1H), 2.28 (s, 3H).

Workup

  1. customTo a round bottom flask equipped with a stir bar
  2. customthe organic phase was isolated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo
  7. customThe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-c2406253b18a49ac99b7a4b6f70522dd
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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