Ammonia → Tyr(3-tBu)-NH2

HRID 1988288Notes

Reaction equation

HRID 1988288 reaction equation
[NH2:1][C@H:2]([C:15]([O:17]C)=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[NH3:19]>>[NH2:1][C@H:2]([C:15]([NH2:19])=[O:17])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 15549498Tyr(3-tBu)-OMe

Product 1

HCID 131722727Tyr(3-tBu)-NH2Yield 80%

Procedure

A mixture of Tyr(3-tBu)-OMe (12.4 g, 49 mmol) and concentrated aqueous ammonia (240 ml) was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the thus obtained residue was subjected to silica gel column chromatography (CHCl3:MeOH=10:1), giving Tyr(3-tBu)-NH2 (T1) (10 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e60d05fbca75477bb2a6876ef19daa63
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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