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

HRID 1270832Notes

Reaction equation

HRID 1270832 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 0.89mL (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-c7dbea557eab465cadb0acc6c615f863
Source dataset
uspto-grants-2007_04
Patent number
US07202381B2

Reaction notes

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