4-Methylmorpholine → HCID 66575075, compound

HRID 1441723Notes

Reaction equation

HRID 1441723 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:5]([OH:18])[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=1.[O:26]=[C:27]1[N:38]([C@@H:39]([CH3:43])[C:40](O)=[O:41])[CH2:37][CH2:36][C@@:28]21[N:32]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:30][CH2:29]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>C(Cl)Cl>[CH2:19]([C@H:4]([NH:3][C:40](=[O:41])[C@@H:39]([N:38]1[CH2:37][CH2:36][C@:28]2([N:32]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:30][CH2:29]2)[C:27]1=[O:26])[CH3:43])[C@H:5]([OH:18])[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:16])[CH3:17])[CH:10]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68679576HCID 68679576, compoundHCID 68682826HCID 68682826, compound

Product 1

HCID 66575075HCID 66575075, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 100 mg (2R,3S)-3-amino-1-(3-isopropyl-benzylamino)-4-phenyl-butan-2-ol dihydrochloride, 79 mg (S)-2-((S)-6-oxo-1-propyl-1,7-diaza-spiro[4.4]non-7-yl)-propionic acid, 102 mg TBTU and 0.171 mL N-methyl morpholine in 5 mL CH2Cl2 is stirred for 5 h at ambient temperature. The solution is diluted with DCM and subsequently washed with bicarbonate, brine, 0.1N HCl and bicarbonate. After drying with MgSO4 all volatiles are evaporated in vacuo and the product is purified by column chromatography (silica gel, DCM/MeOH 95:5) to give 53 mg (37%) of the desired product.

Workup

  1. washsubsequently washed with bicarbonate, brine, 0.1N HCl and bicarbonate
  2. dry with materialAfter drying with MgSO4 all volatiles
  3. customare evaporated in vacuo
  4. customthe product is purified by column chromatography (silica gel, DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-e410c5e28a4d46e1b13eb2f9e646968e
Source dataset
uspto-grants-2010_02
Patent number
US07655686B2

Reaction notes

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