Triphenylphosphine → HCID 21310745, compound

HRID 583395Notes

Reaction equation

HRID 583395 reaction equation
[OH:1][NH:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1.Cl[C:13]1[CH:45]=[CH:44][C:16]([CH2:17][N:18]([S:30]([C:33]2[S:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:36][CH:37]=2)(=[O:32])=[O:31])C2C(C)=CC=CC=2C(NO)=O)=CC=1.[CH3:46][C:47]1C=C(C=[CH:53][C:54]=1C)CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:13][C:45]1[CH:44]=[C:16]([CH:46]=[CH:47][C:54]=1[CH3:53])[CH2:17][N:18]([S:30]([C:33]1[S:34][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[CH:36][CH:37]=1)(=[O:31])=[O:32])[C:5]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([NH:2][OH:1])=[O:11]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 234073,4-Dimethylbenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4288771N-hydroxy-3-methyl-benzamideHCID 21310750HCID 21310750, compound

Product 1

HCID 21310745HCID 21310745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of (5-pyridin-2-yl-thiophene-2-sulfonyl)-amino]-N-hydroxy-3-methyl-benzamide on Wang resin, the product of Example 407 (100 mg, 0.84 mmol/g), in a solution of 3,4 dimethylbenzyl alcohol (0.485 mmol) in THF (1 mL) was added a solution of triphenylphosphine (0.485 mmol) and diethyl azodicarboxylate (0.485 mmol) in THF (1.24 mL). The resultant mixture was shaken for 4 h at room temperature. The resin was filtered, washed with THF (4×3 mL) and dichloromethane (4×3 mL), and dried under vacuum. The resin was suspended in trifluoroacetic acid/ dichloromethane (1:1, 2 mL) and allowed to sit for 1 h. The resin was filtered and washed with DCM (2×1.5 mL). The combined filtrates were evaporated to dryness, and the crude product was purified on a solid phase extraction cartridge (reverse phase) to give 18.1 mg of product Mass Spec: expected 507.1286, found 507.9.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with THF (4×3 mL) and dichloromethane (4×3 mL)
  3. customdried under vacuum
  4. filtrationThe resin was filtered
  5. washwashed with DCM (2×1.5 mL)
  6. customThe combined filtrates were evaporated to dryness
  7. customthe crude product was purified on a solid phase extraction cartridge (reverse phase)

Sources & evidence

ORD record
ord-f8d0e4878c4a469c837d966904374afd
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

Loading…