Methane → (S)-2-(((benzyloxy)carbonyl)(methyl)amino)-3-(4-(benzyloxy)phenyl)propanoic acid

HRID 542650Notes

Reaction equation

HRID 542650 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:30]([OH:32])=[O:31])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:33]I.C>O1CCCC1.O.C(OCC)(=O)C>[CH2:3]([O:10][C:11]([N:13]([CH3:33])[C@H:14]([C:30]([OH:32])=[O:31])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 47600Z-Tyr(Bzl)-OH

Product 1

HCID 13851003(S)-2-(((benzyloxy)carbonyl)(methyl)amino)-3-(4-(benzyloxy)phenyl)propanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of sodium hydride (50%, 9.64 g., prewashed with tetrahydrofuran to remove mineral oil) and tetrahydrofuran (120 ml.) were added dropwise with stirring first a filtered solution of N-benzyloxycarbonyl-O-benzyl-L-tyrosine (16.22 g.) in tetrahydrofuran (50 ml.), then methyl iodide (20 ml.), then tetrahydrofuran (10 ml.). The resulting mixture was stirred overnight at room temperature. Ethyl acetate (200 ml.) was added, then water (6 ml.) dropwise, and stirring was continued for one hour. Charcoal was added and the mixture was filtered. Water (70 ml.) and ether were added, affording a pale yellow solid which melted upon drying at 65° C. and resolidified upon cooling (15.72 g., m.r. 88°-90° C.). Recrystallization of the solid from ethyl acetate (12 ml., 5 ml. used for washing) afforded N-benzyloxycarbonyl-N-methyl-O-benzyl-L-tyrosine (14.13 g.; m.r. 90°-91.5° C.).

Workup

  1. additionwere added dropwise
  2. waitwas continued for one hour
  3. filtrationthe mixture was filtered
  4. additionWater (70 ml.) and ether were added
  5. customaffording a pale yellow solid which
  6. customupon drying at 65° C.
  7. temperatureupon cooling (15.72 g., m.r. 88°-90° C.)
  8. customRecrystallization of the solid from ethyl acetate (12 ml., 5 ml. used for washing)

Sources & evidence

ORD record
ord-76899ea387164f1aafdf682ffb62a1bd
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

Loading…