1,2-Dichloroethane → HCID 118006503, compound

HRID 1486799Notes

Reaction equation

HRID 1486799 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:13])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:14][C@@H:15]([CH2:19][CH3:20])[C:16](O)=[O:17].C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:6]([O:5][CH2:4][C@H:3]([OH:13])[CH2:2][NH:1][C:16](=[O:17])[C@@H:15]([Cl:14])[CH2:19][CH3:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 10786422-Propanol, 1-amino-3-(phenylmethoxy)-, (R)-HCID 6999872(S)-2-Chlorobutyric Acid

Product 1

HCID 118006503HCID 118006503, compoundYield 5.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Preparation of 886355 using modifications to Scheme 7 and Scheme 4: To a stirred solution of (R)-1-amino-3-(benzyloxy)propan-2-ol, Compound 22 in Scheme 7 (8.0 g, 44.1 mmol) in DMF (60 mL) was added (S)-2-chlorobutanoic acid (5.0 g, 40.8 mmol) followed by TEA (10.5 g. 103.8 mmol), DMAP (0.4 g, 3.3 mmol) and finally EDC (9.52 g, 49.7 mmol). The reaction mixture was stirred at rt for 5 d after which time the completed reaction was concentrated to a crude syrup. Purification over silica gel (Biotage, eluting with a gradient of 20-100% EtOAc in heptanes) followed by collection of the desired fractions, concentration and drying in vacuo provided (S)—N—((R)-3-(benzyloxy)-2-hydroxypropyl)-2-chlorobutanamide (683.5 mg, 2.392 mmol, 5.9% yield).

Workup

  1. customPreparation of 886355 using modifications to Scheme 7 and Scheme 4
  2. customthe completed reaction
  3. concentrationwas concentrated to a crude syrup
  4. customPurification over silica gel (Biotage
  5. washeluting with a gradient of 20-100% EtOAc in heptanes)
  6. customfollowed by collection of the desired
  7. concentrationfractions, concentration
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-18aa065fb1cc4451884da3b45ae092a1
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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