Hydrochloric Acid → methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochloride

HRID 1976947Notes

Reaction equation

HRID 1976947 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])=[O:22])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.Cl.C(OCC)C>O1CCOCC1>[ClH:29].[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]2[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])=[O:22])=[CH:18][CH:19]=1)[NH2:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54393861(S)-2-tert-butoxycarbonylamino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

Product 1

HCID 23383932methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochlorideYield 203.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (1.86 g, 4.0 mmol) was treated with 10 mL of 4 N hydrochloric acid in dioxane at room temperature. After 5 minutes, the solid went into solution and the mixture was stirred for 1 hr and 25 mL of ethyl ether was added to precipitate the product. The solids were collected by filtration and were washed with hexane. The resulting hydroscopic and gummy solids were dissolved in 50 mL of methanol and concentrated. After drying under high vacuum, 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester hydrochloride salt (1.64 g, 97%) was obtained as a light yellow solid, mp 158-161° C.

Workup

  1. customto precipitate the product
  2. filtrationThe solids were collected by filtration
  3. washwere washed with hexane
  4. dissolutionThe resulting hydroscopic and gummy solids were dissolved in 50 mL of methanol
  5. concentrationconcentrated
  6. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-aa7e72097def478f9b7bb503c2131ea7
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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