4-Methylmorpholine → HCID 86748618, compound

HRID 1489478Notes

Reaction equation

HRID 1489478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][NH:15][C:16]([CH2:18][C@H:19]([NH:30][S:31]([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)(=[O:33])=[O:32])[C:20]([N:22]([CH2:26][C:27]([OH:29])=O)[CH:23]2[CH2:25][CH2:24]2)=[O:21])=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:45][O:46][NH2:47].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[CH:23]1([N:22]([CH2:26][C:27](=[O:29])[NH:47][O:46][CH3:45])[C:20]([C@@H:19]([NH:30][S:31]([C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=2)(=[O:33])=[O:32])[CH2:18][C:16]([NH:15][CH2:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9]2)=[O:17])=[O:21])[CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 53908337HCID 53908337, compound

Product 1

HCID 86748618HCID 86748618, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg of [[(S)-3-[(S)-1-tert-butoxycarbonyl-piperidin-3-ylmethylcarbamoyl]-2-(naphthalen-2-sulfonylamino)-propionyl]-cyclopropyl-amino]-acetic acid are stirred at room temperature for 20 hours in 10 ml of methylene chloride together with 71 mg of O-methylhydroxylamine hydrochloride, 0.28 ml of N-methyl-morpholine and 376 mg of BOP. The mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and then with water. After drying and evaporation the product is purified over silica gel with ethyl acetate/methanol (9:1). There are obtained 282 mg of tert-butyl (S)-3-[(S)-3-([cyclopropyl-methoxycarbamoylmethyl-carbamoyl)]-3-(naphthalen-2-ylsulfonylamino)-propionylamino-methyl]-piperidine-1-carboxylate, MS (ISP): 646.6 (M+H).

Workup

  1. washwashed with 1N hydrochloric acid
  2. customAfter drying
  3. customevaporation the product
  4. customis purified over silica gel with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-2ce438daa8e84da4bdedeffd0b2edf5b
Source dataset
uspto-grants-1997_10
Patent number
US05677448

Reaction notes

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