Hydrochloric Acid → 3-(4-Acetoxy-2,6-dimethyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

HRID 1823937Notes

Reaction equation

HRID 1823937 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=1[CH3:22])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:25](OC(=O)C)(=[O:27])[CH3:26].Cl>>[C:25]([O:21][C:17]1[CH:16]=[C:15]([CH3:22])[C:14]([CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11])=[C:19]([CH3:20])[CH:18]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 13656656Boc-L-2,6-Dimethyltyrosine

Product 1

HCID 221476663-(4-Acetoxy-2,6-dimethyl-phenyl)-2-tert-butoxycarbonylamino-propionic acid

Procedure

To a solution of 0.77 g (2.5 mmol) of 2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid and 3 mL of 3N sodium hydroxide solution, cooled in an ice bath, was added 0.89 mL (9.4 mmol) of acetic anhydride dropwise over about 30 seconds. After stirring for 2 hours, the mixture was acidified with addition of 4.5 mL of 2N hydrochloric acid. The mixture was extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrate to a clear oil. The title product was used for the next reaction without further purification.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrate to a clear oil
  4. customThe title product was used for the next reaction without further purification

Sources & evidence

ORD record
ord-aef1bcaf8f724f9b8d32d125f0a45551
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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