1,2-Dichloroethane → HCID 22053947, compound

HRID 1830175Notes

Reaction equation

HRID 1830175 reaction equation
N1(C(=O)C[CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=O)CCOCC1.[OH:25][C:26](C(F)(F)F)=O.[NH2:32][CH:33]([CH2:44][CH3:45])[C:34]([C:36]1[O:37][C:38]([CH2:41][O:42][CH3:43])=[N:39][N:40]=1)=[O:35].[CH:46]1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C[N:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1>C(Cl)Cl>[OH:35][CH:34]([C:36]1[O:37][C:38]([CH2:41][O:42][CH3:43])=[N:39][N:40]=1)[CH:33]([NH:32][C:26](=[O:25])[C:13]([CH3:46])([S:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:15])=[O:16])[CH2:9][C:10]([N:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1)=[O:12])[CH2:44][CH3:45]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539874-Morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acidHCID 86611136HCID 86611136, compound

Product 1

HCID 22053947HCID 22053947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acid (230 mg, 0.65 mmol), 2-amino-1-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-butan-1-one TFA salt (204 mg), prepared as in reference 15, and HOBt (119 mg, 0.78 mmol) in MeCl2 (5 ml), was added EDC (187 mg, 0.98 mmol) and N-methylmorpholine (0.35 ml) at room temperature. After stirring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated to yield 82 mg of N-{1-[Hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide; MS: 537.6(M−1), 539.8 (M+1).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2c51fcb893ce4f918f94f946f6db1669
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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