Ethylmorpholine → HCID 66919717, compound

HRID 1971686Notes

Reaction equation

HRID 1971686 reaction equation
[CH:1]([N:4]1[C:32](=[O:33])[C:31]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])=[CH:19][C:20]=4[C:11]3=[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[C:9]=2[CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[F:39][C:40]([F:47])([F:46])[CH2:41][CH2:42][C:43](O)=[O:44].C(N1CCOCC1)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(OCC)(=O)C.O>[CH:1]([N:4]1[C:32](=[O:33])[C:31]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])=[CH:19][C:20]=4[C:11]3=[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[C:9]=2[CH2:8][N:7]([C:43](=[O:44])[CH2:42][CH2:41][C:40]([F:47])([F:46])[F:39])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27770854,4,4-Trifluorobutanoic acidHCID 58124924HCID 58124924, compound

Product 1

HCID 66919717HCID 66919717, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 26 mg of 10q, 10 mg of trifluorobutyric acid, 15 μl of N-ethyl morpholine and 20 mg of TBTU was stirred at RT for 1 hr. The turbid mixture readily became homogeneous. After one hour, water and ethyl acetate were added and the mixture was stirred for ½ hr. The organic layer was once washed with 1N NaOH and twice with 5% aq. NH4Cl, dried and concentrated. The residue was treated with diethyl ether, from which 25 mg of 10t crystallized, Mp: 256-258° C. Rf 0.25 (heptane/acetone). MS-ESI: [M+1] 654.18

Workup

  1. waitAfter one hour
  2. stirringthe mixture was stirred for ½ hr
  3. washThe organic layer was once washed with 1N NaOH and twice with 5% aq. NH4Cl
  4. customdried
  5. concentrationconcentrated
  6. additionThe residue was treated with diethyl ether, from which 25 mg of 10t
  7. customcrystallized

Sources & evidence

ORD record
ord-0f3e611b96524f409fe5077e899048a9
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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