4-Methylmorpholine → HCID 131719245, compound

HRID 375103Notes

Reaction equation

HRID 375103 reaction equation
[NH:1]([C:18]([O:20]C(C)(C)C)=O)[C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].CN1CCOCC1.C(OC(=O)[C@@H:41]([N:57]=[N+:58]=[N-:59])[C:42]1([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43]1)C1C=CC=CC=1.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(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:11]([O:10][C:8](=[O:9])[C@@H:2]([NH:1][C:18](=[O:20])[C@@H:41]([N:57]=[N+:58]=[N-:59])[C:42]1([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43]1)[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10688217HCID 10688217, compoundHCID 54399356HCID 54399356, compound

Product 1

HCID 131719245HCID 131719245, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Boc-γMeLeu-OBzl (0.272 g, 0.81 mmol) in 30% TFA in CH2Cl2 was stirred at 0° for 1 h. The solvent was evaporated and the residue was dried under vacuum. The resulting TFA salt was dissolved in acetonitrile (20 mL). NMM (0.53 mL, 4.86 mmol) was added to the solution, followed by the addition of (S)-α-azido-1-[(phenylmethoxy)carbonyllcyclo-pentaneacetic acid (0.269 g, 0.89 mmol, described in example 7) and BOP (0.464 g, 1.05 mmol). The mixture was stirred at room temperature for 18h. The solvent was evaporated. The residue was dissolved in EtOAc (50 mL). The solution was washed with 10% aqueous HCl (2×25 mL), a sainted aqueous solution of Na2CO3 (2×25 mL) and brine (25 mL). Evaporation of the organic phase gave N-{(S)-α-azido-1-[(phenylmethoxy)-carbonyl]cyclopentaneacetyl}-2(S)-amino-4,4-dimethylpentanoic acid benzyl ester as a yellow oil (0.400 g, 96% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was dried under vacuum
  3. dissolutionThe resulting TFA salt was dissolved in acetonitrile (20 mL)
  4. customThe solvent was evaporated
  5. dissolutionThe residue was dissolved in EtOAc (50 mL)
  6. washThe solution was washed with 10% aqueous HCl (2×25 mL)
  7. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-ddd6a0922c7c4cf0bde009d1af3216d6
Source dataset
uspto-grants-1996_01
Patent number
US05484771

Reaction notes

Loading…