Triethylamine → HCID 59732428, compound

HRID 131637Notes

Reaction equation

HRID 131637 reaction equation
[OH:1][C@:2]1([CH3:35])[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH:21]([CH3:23])[CH3:22])[C:12]=3[S:11][C:10]=2[CH2:24][C:25]2[C:26]([C:31]([F:34])([F:33])[F:32])=[N:27][NH:28][C:29]=2[CH3:30])=[O:8])[CH2:3]1.Cl.C[C@]1(O)CONC1.[N+](C1C=C(S(OC[C@@]2(C)CO2)(=O)=O)C=CC=1)([O-])=O.C(N(CC)CC)C>C1COCC1>[OH:1][C@@:2]1([CH3:35])[CH2:6][O:5][N:4]([C:7]([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH:21]([CH3:22])[CH3:23])[C:12]=3[S:11][C:10]=2[CH2:24][C:25]2[C:26]([C:31]([F:32])([F:33])[F:34])=[N:27][NH:28][C:29]=2[CH3:30])=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10369242AZD3965HCID 57463982HCID 57463982, compoundHCID 68962815(R)-4-Methylisoxazolidin-4-ol hydrochloride

Product 1

HCID 59732428HCID 59732428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the product of example 10 part a) (0.130 mg) and (4R)-4-methyl-4-isoxazolidinol hydrochloride (42 mg, prepared by the method of example 1 steps a) to d) using [(2R)-2-methyloxiran-2-yl]methyl 3-nitrobenzenesulfonate) in anhydrous THF (6 ml), was added triethylamine (120 mg) and the mixture was cooled in an icebath. O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetamethyluronium hexafluorophosphate (120 mg) was added and the mixture was allowed to warm to, whereupon it was stirred for 3 hr. All volatiles were removed in vacuo and the residue was chromatographed (SiO2/1:1 CH2Cl2-EtOAc) to effect primary purification. Further purification by RPHPLC afforded the title compound as a solid (35 mg).

Workup

  1. customprepared by the method of example 1 steps a)
  2. temperaturethe mixture was cooled in an icebath
  3. temperatureto warm to, whereupon it
  4. customAll volatiles were removed in vacuo
  5. customthe residue was chromatographed (SiO2/1:1 CH2Cl2-EtOAc)
  6. custompurification
  7. customFurther purification by RPHPLC

Sources & evidence

ORD record
ord-0a3c58f293b3418fbc5e8edc055891b0
Source dataset
uspto-grants-2008_06
Patent number
US07384951B2

Reaction notes

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