Dimethylformamide → HCID 131718328, compound

HRID 1974903Notes

Reaction equation

HRID 1974903 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:2]([C:14](O)=[O:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[CH:5]=1.[CH:24]1[CH:25]=[CH:26][C:27]2N(O)N=N[C:28]=2[CH:29]=1.CN([CH:37]=[O:38])C>>[NH:1]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[C@@H:2]([C:14]([NH:1][C@@H:2]([C:14]([O:38][CH3:37])=[O:15])[CH2:3][C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:29]=1)=[O:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[CH:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 13821420HCID 13821420, compound

Product 1

HCID 131718328HCID 131718328, compound

Procedure

To a mixture of Boc-D-Trp(CH3)-OH (1.59 g), HCl·H-D-Phe-OCH3 (1.08 g) and HOBT (0.81 g) in DMF (20 ml) was added WSCD (0.93 g) under ice-bath cooling. After being stirred for 2 hours at room temperature, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (50 ml). The solution was washed with 0.5N hydrochloric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml) and water (20 ml×2) successively, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ether to give Boc-D-Trp(CH3)-D-Phe-OCH3 (1.45 g).

Workup

  1. additionwas added WSCD (0.93 g) under ice-bath
  2. temperaturecooling
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  5. washThe solution was washed with 0.5N hydrochloric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml) and water (20 ml×2) successively
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-257af4d13ac04aeda5567cebca8b1d48
Source dataset
uspto-grants-1994_02
Patent number
US05284828

Reaction notes

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