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

HRID 1282604Notes

Reaction equation

HRID 1282604 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 hydrochloride

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 4 N hydrochloric acid in dioxane (10 mL) at room temperature. After 5 minutes, the solids went into solution and the mixture was stirred for 1 h. Then, 25 mL of ethyl ether was added to precipitate the product. The solids were collected by filtration and washed with hexane. The resulting solid was very hydroscopic and became gummy. This material was 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. washwashed with hexane
  4. dissolutionThis material was dissolved in 50 mL of methanol
  5. concentrationconcentrated
  6. dry with materialAfter drying under high vacuum, 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester hydrochloride salt
  7. custom(1.64 g, 97%) was obtained as a light yellow solid

Sources & evidence

ORD record
ord-82b66554669f42699a09b0ce1508bda6
Source dataset
uspto-grants-2002_09
Patent number
US06455550B1

Reaction notes

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