Tert-butoxycarbonylalanine → HCID 22877896, compound

HRID 1488860Notes

Reaction equation

HRID 1488860 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[N:28]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH:54]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C@H:55]([C:57](O)=[O:58])[CH3:56].C(=O)([O-])O.[Na+]>C(#N)C.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:60]([NH:54][C@H:55]([C:57]([NH2:28])=[O:58])[CH3:56])([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61]

Participants

8

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 9976854HCID 9976854, compound

Product 1

HCID 22877896HCID 22877896, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride (1,053 mg, 2.65 mmols), 1,300 mg of a BOP reagent and 554 mg of Boc-L-Ala were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at 60° C. for 17 hours. One-hundred milliliters of water and a small amount (about 10 g) of sodium hydrogencarbonate were added thereto, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, mixture of dichloromethane and ethyl acetate at a ratio of 20:1), and then concentrated to produce 1,085 mg (2.12 mmols) of the final product in a yield of 80%.

Workup

  1. customThe mixture was reacted at 60° C. for 17 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified
  7. additioneluent, mixture of dichloromethane and ethyl acetate at a ratio of 20:1), and
  8. concentrationthen concentrated

Sources & evidence

ORD record
ord-e0f0e0e4ace74e749050faf05b8838da
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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