4-Methylmorpholine → HCID 69313194, compound

HRID 751466Notes

Reaction equation

HRID 751466 reaction equation
Cl.[NH2:2][CH:3]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][N:6]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)(=[O:14])=[O:13])[CH2:5][CH:4]1[OH:21].[NH:22]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:23]([C:28](O)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:34]([O:33][C:31](=[O:32])[NH:22][C@H:23]([C:28](=[O:29])[NH:2][CH:3]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][N:6]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)(=[O:14])=[O:13])[CH2:5][CH:4]1[OH:21])[CH2:24][CH:25]([CH3:26])[CH3:27])([CH3:35])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69313092HCID 69313092, compound

Product 1

HCID 69313194HCID 69313194, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-6,6-dimethyl-1-(pyridine-2-sulfonyl)-azepan-3-ol HCl salt from Example 92g (0.22 g, 0.6 mmol) was dissolved in 5 ml DMF. To this solution, was added Boc-Leu-OH (0.22 g, 0.9 mmol) and HBTU (0.34 g, 0.9 mmol) and then NMM (0.24 g, 2.4 mmol). The mixture was stirred at r.t. overnight. DMF was removed under high vacuum. The residue was diluted with EtOAc and washed with H2O, 10% NaHCO3 and brine. Purification by column chromatography gave 0.22 g of the title compound (72% yield); MS (M+H+): 512.9; 1H-NMR (400 MHz, CDCl3): •8.68-8.67(d, 1H), 7.97-7.88(m, 2H), 7.69-7.64(m, 1H), 6.62-6.53(m, 1H), 5.06-5.00(m, 1H), 4.03-3.18(m, 7H), 1.80-1.42(m, 15H), 1.04-0.92(m, 12H).

Workup

  1. customDMF was removed under high vacuum
  2. additionThe residue was diluted with EtOAc
  3. washwashed with H2O, 10% NaHCO3 and brine
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-e6816c372d014894b58eadb33aeb5bce
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

Loading…