Dicyclohexylcarbodiimide → HCID 178449796, compound

HRID 1819376Notes

Reaction equation

HRID 1819376 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCC(N=C=NC2CCCCC2)CC1.Cl.Cl.[NH2:33][C:34]1[NH:35][C:36]2[NH:37][CH2:38][CH:39]([CH:45]([OH:49])[CH:46]([OH:48])[CH3:47])[NH:40][C:41]=2[C:42](=[O:44])[N:43]=1>C(Cl)Cl.N1C=CC=CC=1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]([C:13]([N:40]1[CH:39]([CH:45]([OH:49])[CH:46]([OH:48])[CH3:47])[CH2:38][NH:37][C:36]2[NH:35][C:34]([NH2:33])=[N:43][C:42](=[O:44])[C:41]1=2)=[O:15])[CH:10]([CH3:11])[CH3:12])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 178469707HCID 178469707, compound

Product 1

HCID 178449796HCID 178449796, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-Boc-L-Valine (4.56 g, 21 mmol) in DCM (15 ml) at 0° C. was added a solution of DCC (2.17 g, 10.5 mmol) in DCM (10 ml). The resulting solution was stirred for 1 h after which a white precipitate formed. The white solid was filtered and filtrate added to a stirred solution of 2-amino-6-(1,2-dihydroxy-propyl)-5,6,7,8-tetrahydro-1H-pteridin-4-one dihydrochloride (3.0 g, 9.55 mmol) dissolved in pyridine (80 mL). The mixture was stirred at room temperature under an atmosphere of nitrogen for 1.5 h. The reaction mixture was quenched by addition of methanol (20 ml). The solvent was evaporated in vacuo and the residue purified by preparative RP-HPLC to give the sub-title product as a tan solid (3.2 g, 76%). MS: ESI (positive): 441 (M+H).

Workup

  1. customformed
  2. filtrationThe white solid was filtered
  3. stirringThe mixture was stirred at room temperature under an atmosphere of nitrogen for 1.5 h
  4. customThe reaction mixture was quenched by addition of methanol (20 ml)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-2ce232660ebf4eab905e688676f6df47
Source dataset
uspto-grants-2009_10
Patent number
US07601717B2

Reaction notes

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