1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

HRID 16371Notes

Reaction equation

HRID 16371 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:25])[C@H:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][O:12][CH2:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:29]([CH2:33]C)C(C)C)(C)C.Cl.CN[O:38][CH3:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:21]([O:20][C:18](=[O:19])[NH:17][C@H:10]([CH2:11][O:12][CH2:13][C:14](=[O:16])[NH:29][CH2:33][O:38][CH3:39])[C@H:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:25])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 67373378((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid

Product 1

HCID 67379173{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid (42.1 g) in DMF (400 mL) was successively added N,N-diisopropylethylamine (41 mL), N,O-dimethylhydroxyamine hydrochloride (17.4 g), EDCI (34.3 g) and HOBt (24.1 g), and the resultant solution was stirred for 16 hours at room temperature. Solvent was removed by distillation under reduced pressure, and the resultant product was diluted with ethyl acetate and water. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure. After passing the residue through a silica pad (silica gel 500 cc), the filtrate was concentrated by distillation under reduced pressure, to thereby obtain the titled compound (46.0 g). The physical properties of the compound were as follows.

Workup

  1. customSolvent was removed by distillation under reduced pressure
  2. additionthe resultant product was diluted with ethyl acetate and water
  3. customThe organic layer was partitioned
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customSolvent was removed by distillation under reduced pressure
  7. concentrationthe filtrate was concentrated by distillation under reduced pressure

Sources & evidence

ORD record
ord-6acb6780b90244fb9f07bbaa5a2fe621
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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