Water → HCID 131715065, compound

HRID 1761362Notes

Reaction equation

HRID 1761362 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][C@H:4]([NH:8][S:9]([C:12]1[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:5](=[O:7])[CH3:6].[C:20]([O:24][CH2:25][Li])([CH3:23])([CH3:22])[CH3:21].O>C1COCC1>[C:20]([O:24][CH2:25][C:5]([CH3:6])([OH:7])[CH:4]([NH:8][S:9]([C:12]1[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:3][CH:2]([CH3:19])[CH3:1])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 70091302HCID 70091302, compoundHCID 178506883HCID 178506883, compound

Product 1

HCID 131715065HCID 131715065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a -78° C. solution of the resultant compound of Example 57 (1.0 g, 3.5 mmol) in dry THF (7 ml) was added 3 equivalent, of t-butoxymethyl lithium [E. J. Corey and T. M. Eckridge, Tetrahedron Letters, 3165 (1983)]. The mixture was warmed to room temperature for 4 hours and then poured into water. Acidification with 0.1 M H3PO4, extraction into ether, washing with brine, drying, and evaporating gave 1.1 (85%) of the desired compound. Mass spectrum: M+ =371.

Workup

  1. extractionAcidification with 0.1 M H3PO4, extraction into ether
  2. washwashing with brine
  3. customdrying
  4. customevaporating

Sources & evidence

ORD record
ord-1e8f33bc3ff0433a9419ad22cf11c7ff
Source dataset
uspto-grants-1989_05
Patent number
US04826815

Reaction notes

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