Hydrochloric Acid → HCID 66618432, compound

HRID 2200309Notes

Reaction equation

HRID 2200309 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:24][CH2:23]1)[CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])=O)(C)(C)C.Cl>C(Cl)Cl>[ClH:20].[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C@@H:10]([CH2:9][NH:8][CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:11]([OH:13])=[O:12])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66618045(S)-3-(tert-butoxycarbonyl(cyclopropylmethyl)amino)-2-(4-chlorophenyl)propanoic acid

Product 1

HCID 66618432HCID 66618432, compoundYield 190.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude (S)-3-(tert-butoxycarbonyl(cyclopropylmethyl)amino)-2-(4-chlorophenyl)propanoic acid (4.6 g, 13 mmol) was dissolved into DCM (130 mL) and excess 4N HCl was added. The reaction was allowed to stir overnight, after which it was concentrated. The resulting white solid was taken up into EtOAC and filtered. The resulting solid was washed with EtOAc (4×) to give pure (S)-2-(4-chlorophenyl)-3-(cyclopropylmethylamino)propanoic acid hydrochloride (3.60 g, 95%). This (S)-2-(4-chlorophenyl)-3-(cyclopropylmethylamino)propanoic acid (0.57 g, 2.24 mmol) was dissolved into 10:1 CH3CN:H2O (50 mL) and tetramethylammonium hydroxide pentahydrate (1.00 g) was added followed by Boc2O (0.73 g, 3.36 mmol). The reaction mixture was allowed to stir at room temperature overnight, and the reaction was quenched by the addition of 1N HCl. The reaction was concentrated, and the residue was diluted with EtOAc. The organics were separated, and the aqueous portion was extracted with EtOAc. The combined organics were dried with MgSO4, filtered and concentrated. The crude residue was purified by silica plug eluting Hex to 1:1 Hex/EtOAc to give (S)-3-(tert-butoxycarbonyl(cyclopropylmethyl)amino)-2-(4-chlorophenyl)propanoic acid (0.58 g, 73%) as a clear oil. (LCMS (APCI+) [M−Boc+H]+ 254.0)

Workup

  1. additionwas added
  2. concentrationafter which it was concentrated
  3. filtrationfiltered
  4. washThe resulting solid was washed with EtOAc (4×)

Sources & evidence

ORD record
ord-0ae1929c2206452cb30055d8ef5f8b6e
Source dataset
uspto-grants-2016_06
Patent number
US09359340B2

Reaction notes

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