Lithium Hydroxide → HCID 53706294, compound

HRID 1699268Notes

Reaction equation

HRID 1699268 reaction equation
C[N:2]([C:17]([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[O:18])[C@@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([OH:12])=[C:7]([Br:13])[CH:6]=1.[OH-].[Li+]>O>[Br:11][C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([Br:13])[C:8]=1[OH:12])[CH2:4][C@H:3]([C:14]([OH:16])=[O:15])[NH:2][C:17]([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[O:18]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68853991HCID 68853991, compound

Product 1

HCID 53706294HCID 53706294, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 24 g (46.3 mmol) of methyl 3,5-dibromo-N-[[[2-(3-methoxyphenyl)ethyl]amino]carbonyl]-D-tyrosine and 5.0 g (50 mmol) of lithium hydroxide in 200 ml of water was stirred for 1 hour at 60 C. The solid product was suction filtered and the filtrate was washed with 200 ml of ethyl acetate. By the addition of 1 M aqueous hydrochloric acid the aqueous phase was adjusted to a pH of 3-4 and extracted 3 times with 150 ml of ethyl acetate. The combined ethyl acetate phases were washed once with water, dried over sodium sulphate and evaporated down in vacuo. The residue was triturated with ether. 9.1 g (38% of theory) of a colourless solid were obtained.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with 200 ml of ethyl acetate
  3. additionBy the addition of 1 M aqueous hydrochloric acid the aqueous phase
  4. extractionextracted 3 times with 150 ml of ethyl acetate
  5. washThe combined ethyl acetate phases were washed once with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated down in vacuo
  8. customThe residue was triturated with ether
  9. custom9.1 g (38% of theory) of a colourless solid were obtained

Sources & evidence

ORD record
ord-3c58c50ba46043e3bb681b9cb334e5d6
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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