4-Methylmorpholine → Tyrosine N'-Boc-hydrazide

HRID 847271

Reaction equation

HRID 847271 reaction equation
C([NH:11][C@H:12]([C:21]([OH:23])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)(OCC1C=CC=CC=1)=O.CN1CCOCC1.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[NH:32][NH2:33]>O1CCCC1>[C:31]([NH:32][NH:33][C:21](=[O:23])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[NH2:11])([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 70091tert-Butyl carbazateHCID 712438N-benzyloxycarbonyl-l-tyrosine

Product 1

HCID 22845507Tyrosine N'-Boc-hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of CBZ-L-tyrosine (3.00 gm, 9.11 mmoles), N-methylmorpholine (0.92 gm, 1.00 ml, 9.11 mmoles) in 100 ml dry tetrahydrofuran (THF) was cooled to 0° C. under nitrogen. 2,2,2-Trichloro-1,1-dimethylethylchloroformate (2.18 gm, 9.11 mmoles) was added to the cold solution. After 5 minutes stirring, a solution of t-butyl carbazate (1.20 gm, 9.11 mmoles) in 20 ml dry THF was cooled to 0° C. and added to the reaction mixture. The mixture was allowed to warm slowly to room temperature and was stirred for about 18 hours. The solvent was removed by rotary evaporation and the residue was partitioned between chloroform and water and the layers separated. The organic layer was washed with saturated NaCl dried over Na2SO4, filtered, and solvent evaporated to yield the crude protected product. The CBZ-protected product, CBZ-tyrosine N'-Boc-hydrazide, was purified on silica gel via flash chromatography using a mixture of petroleum ether and ethyl acetate (1:1).

Workup

  1. additionadded to the reaction mixture
  2. stirringwas stirred for about 18 hours
  3. customThe solvent was removed by rotary evaporation
  4. customthe residue was partitioned between chloroform and water
  5. customthe layers separated
  6. washThe organic layer was washed with saturated NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customsolvent evaporated
  10. customto yield the crude protected product
  11. customThe CBZ-protected product, CBZ-tyrosine N'-Boc-hydrazide, was purified on silica gel via flash chromatography
  12. additiona mixture of petroleum ether and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d87efd99412042b991f4e3eb41a8f29a
Source dataset
uspto-grants-1992_08
Patent number
US05140104

Linked notes

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