Water → HCID 67033352, compound

HRID 876579Notes

Reaction equation

HRID 876579 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@H:7]([O:16][C:17](=[O:19])[CH3:18])[C@@H:8]([O:12][C:13](=[O:15])[CH3:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:25]1[CH:34]=[CH:33][C:28]([NH:29][CH2:30][CH2:31][Cl:32])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].Cl.C(N=C=NCCCN(C)C)C.O>C(Cl)Cl>[C:17]([O:16][C@H:7]([C@@H:8]([O:12][C:13](=[O:15])[CH3:14])[C:9]([N:29]([CH2:30][CH2:31][Cl:32])[C:28]1[CH:27]=[CH:26][C:25]([C:21]([CH3:24])([CH3:22])[CH3:23])=[CH:34][CH:33]=1)=[O:11])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:20])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 141434761-(1,1-Dimethylethyl) (2R,3R)-2,3-bis(acetyloxy)butanedioateHCID 67223625HCID 67223625, compound

Product 1

HCID 67033352HCID 67033352, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R,R)-2,3-bis(acetyloxy)-butanedioic acid mono tert-butyl ester (9 g: Tetrahedron, 45, 3071-3080, 1989) in CH2Cl2 (90 mL), were added compound 11-1 (6.6 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride at 0° C. The reaction mixture was stirred for 5 hours at room temperature. Then water was added into the mixture and it was extracted with CH2Cl2. The organic layer was washed with brine, dried with anhyd. Na2SO4. The solvent was removed under reduced pressure to obtain compound 52-1 (15.8 g) as a brown amorphous solid.

Workup

  1. extractionwas extracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. customdried with anhyd
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-865d8f289fb0475b984eb1dcd1185d69
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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