Diisopropylethylamine → Benzyl[(1S)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate

HRID 269626Notes

Reaction equation

HRID 269626 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:34]([O:41][C:42]([NH:44][C@H:45]([C:48]([OH:50])=O)[CH2:46][OH:47])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:51]([O:55][C:56](=[O:63])[NH:57][CH2:58][CH:59]([OH:62])[CH2:60][NH2:61])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C>[CH2:34]([O:41][C:42](=[O:43])[NH:44][C@@H:45]([CH2:46][OH:47])[C:48]([NH:61][CH2:60][CH:59]([OH:62])[CH2:58][NH:57][C:56]([O:55][C:51]([CH3:53])([CH3:52])[CH3:54])=[O:63])=[O:50])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10511887tert-butyl N-(3-amino-2-hydroxypropyl)carbamate

Product 1

HCID 131727151Benzyl[(1S)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

362.8 mg (0.954 mmol) of HATU and 123.3 mg (0.954 mmol) of N,N-diisopropylethylamine are added to a solution of 207.5 mg (0.867 mmol) of N-[(benzyloxy)carbonyl]-L-serine in 10 ml of anhydrous DMF. After stirring at RT for 15 min, 165 mg (0.867 mmol) of tert-butyl(3-amino-2-hydroxypropyl)carbamate are added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

Workup

  1. stirringThe reaction mixture is stirred at RT for 15 h
  2. customThe solvent is then evaporated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-09a9ce9f7fd141f8bc16ff20e4cd4361
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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