Ethylmorpholine → HCID 86749862, compound

HRID 744900Notes

Reaction equation

HRID 744900 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])[CH:11]([CH2:22][C:23]([OH:25])=O)[C:10]1=[O:26])=[O:7])(C)(C)C.[CH2:27]([N:29]1CCOCC1)C.F[P-](F)(F)(F)(F)F.[N:42]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50]C=2N=N1.Cl.Cl.[C:64](N1CCC[C@@H](CN)C1)(=[NH:66])[NH2:65]>CN(C=O)C>[NH2:66][C:64](=[NH:65])[C@@H:22]([C:23](=[O:25])[NH:29][CH2:27][CH:49]1[CH2:48][CH2:47][CH2:46][NH:42][CH2:50]1)[CH:11]1[N:12]([S:15]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])=[O:17])[CH2:13][CH2:14][N:9]([CH2:8][C:6]([OH:5])=[O:7])[C:10]1=[O:26]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19422613HCID 19422613, compoundHCID 22852514HCID 22852514, compound

Product 1

HCID 86749862HCID 86749862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 g of (RS)-(4-tert-butoxycarbonylmethyl-1-butylsulphonyl-3-oxo-piperazin-2-yl)-acetic acid is dissolved in 15 ml of DMF, treated in succession with 1.3 ml of 4-ethylmorpholine, 0.92 g of BOP and 0.72 g of (S)-1-amidino-3-(aminomethyl)-piperidine dihydrochloride. The reaction mixture is stirred at room temperature overnight, then evaporated and the residue is chromatographed on RP-18 with a water-acetonitrile gradient. The product fractions are evaporated and filtered over an ion exchanger (Cl- form) with water-ethanol. Colourless [3-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethylcarbamoylmethyl]-4-butylsulphonyl-2-oxo-piperazin-1yl]acetic acid (1:1), MS (ion spray): 475.6 (M+H)+, is isolated after evaporation.

Workup

  1. customevaporated
  2. customthe residue is chromatographed on RP-18 with a water-acetonitrile gradient
  3. customThe product fractions are evaporated
  4. filtrationfiltered over an ion exchanger (Cl- form) with water-ethanol

Sources & evidence

ORD record
ord-bb20e79876274b5d8c823f534964028f
Source dataset
uspto-grants-1996_09
Patent number
US05559232

Reaction notes

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