Water → HCID 11397615, compound

HRID 1986353Notes

Reaction equation

HRID 1986353 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:20][C:21]1[C:22]([C:26]2[N:27]([C:46]3[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=3)[C:28]3[CH:33]=[C:32]([O:34][C:35]4[CH:36]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[CH:38]=[CH:39][CH:40]=4)[N:31]=[CH:30][C:29]=3[N:45]=2)=[N:23][O:24][N:25]=1.C([NH:60][CH2:61][CH2:62]O)(OC(C)(C)C)=O.O>O1CCOCC1>[NH2:60][CH2:61][CH2:62][O:52][C:49]1[CH:50]=[CH:51][C:46]([N:27]2[C:28]3[CH:33]=[C:32]([O:34][C:35]4[CH:36]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[CH:38]=[CH:39][CH:40]=4)[N:31]=[CH:30][C:29]=3[N:45]=[C:26]2[C:22]2[C:21]([NH2:20])=[N:25][O:24][N:23]=2)=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 68871617HCID 68871617, compound

Product 1

HCID 11397615HCID 11397615, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triphenylphosphine (260 mg, 1.0 mmol) was added to a solution of the product from Step 5 (220 mg, 0.5 mmol) and N—BOC-ethanolamine (161 mg, 1.0 mmol) in dioxane (4 mL) followed by addition of di-isopropylazodicarboxylate (197 uL, 1.0 mmol) and the resulting solution was allowed to stir at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated. The crude material was dissolved in dichloromethane (2 mL) and treated with TFA (1 mL) for 30 min, then concentrated and the residue was purified by reverse phase HPLC to give the title compound (38 mg, 16%). MS (ES+) m/e 487 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. dissolutionThe crude material was dissolved in dichloromethane (2 mL)
  7. additiontreated with TFA (1 mL) for 30 min
  8. concentrationconcentrated
  9. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-845df6269aa14ad583ad318eba60a5b5
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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