Methanol → HCID 131726474, compound

HRID 1354981Notes

Reaction equation

HRID 1354981 reaction equation
[NH:1]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:2]([C:15](OC)=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C1COCC1.O>[NH:1]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:2]([CH:15]=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 58868037HCID 58868037, compound

Product 1

HCID 131726474HCID 131726474, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

All four stereoisomers of 3 were synthesized according to the following procedure: To a stirred solution of Boc-D-Tyr(tBu)-OMe (2.2 g, 6.3 mmole) in toluene/THF (1:1, 20 mL) at −78° C. under N2 was added DIBAL-H (1.5 M in toluene, 10.4 mL, 15.7 mmole) dropwise over 30 minutes. The reaction was stirred for 30 minutes, then quenched by the slow addition of MeOH (1.3 mL, 31.5 mmole) and warmed to room temperature. Rochelle's salt (9 g, 31.5 mmole) in water (50 mL) was added, and the mixture was stirred for 1 hour, then filtered and extracted with ether (50 mL). The ether extract was dried over MgSO4, filtered, and concentrated under vacuum to give Boc-D-Tyr(tBu)-H.

Workup

  1. customAll four stereoisomers of 3 were synthesized
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationfiltered
  4. extractionextracted with ether (50 mL)
  5. extractionThe ether extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-47095e3c056641eba5c4d30be9679523
Source dataset
uspto-grants-2007_05
Patent number
US07223888B2

Reaction notes

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