MeOH tetrahydrofuran → Tyrosine Methyl Ester

HRID 2117022Notes

Reaction equation

HRID 2117022 reaction equation
[N+](=C[C:4](C=[N+]=[N-])=[O:5])=[N-].NC1SC=[C:13]([C@@H:15]([NH:27]C(OC(C)(C)C)=O)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]C(=O)C)=[CH:19][CH:18]=2)N=1.C1C[O:38]CC1.CO>C(N(CC)CC)C.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[CH3:4][O:5][C:13](=[O:38])[C@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[NH2:27]

Participants

6

Reactant 3

HCID 21899815MeOH tetrahydrofuranHCID 54572627Diazomethyl ketoneHCID 59909973Acetic acid 4-[(S)-2-(2-amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-ethyl]-phenyl ester

Product 1

HCID 70652Tyrosine Methyl Ester

Reagents, catalysts & solvents 2

HCID 164649Silver benzoateCatalystHCID 8471TriethylamineSolvent

Procedure

The diazomethylketone derived from Bis-Boc-Tyr (Example 64, 0.750 g, 1.85 mmol) was dissolved in a 1/1 mixture of THF/MeOH (10 mL). A solution of silver benzoate (50 mg) in triethylamine (1 mL) was added. After 15 min of stirring at room temperature the solvent was evaporated and the residue purified by flash chromatography (gradient 10-25% EtOAc/hexane) to yield 749 mg of protected tyrosine methyl ester.

Workup

  1. customwas evaporated
  2. customthe residue purified by flash chromatography (gradient 10-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-47bbff83a4e94ad7b72487e5cfa6ef70
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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