Water → HCID 69199220, compound

HRID 2118317Notes

Reaction equation

HRID 2118317 reaction equation
[CH3:1][C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:48])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([S:32]([N:35](COCC[Si](C)(C)C)[CH2:36][C:37]([NH2:39])=[O:38])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1.O>C(O)(=O)C.CO.ClCCl>[C:2]([OH:7])(=[O:3])[CH3:1].[OH:48][C@H:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([S:32]([NH:35][CH2:36][C:37]([NH2:39])=[O:38])(=[O:33])=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 962WaterHCID 69452388HCID 69452388, compound

Product 1

HCID 69199220HCID 69199220, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N2-[(3-{4-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide (0.091 g) was stirred under a reflux condenser at 80° in acetic acid (2 ml) and water (1 ml) for 3.5 h. The solution was evaporated to dryness and re-evaporated twice with methanol to give a gum. The residue was dissolved in methanol and loaded onto two 20×20cm preparative silica gel coated plates (1 mm layer). The plates were run in dichloromethane:ethanol:0.880 ammonia solution, 25:8:1 and elution of the main band and evaporation gave a gum. This was dissolved in acetic acid (2 ml) and evaporated to dryness and re-evaporated with methanol to give the title compound (0.019 g) LCMS RT=2.31 min, ES+ve 552 (MH)+.

Workup

  1. customThe solution was evaporated to dryness
  2. customre-evaporated twice with methanol
  3. customto give a gum
  4. washethanol:0.880 ammonia solution, 25:8:1 and elution of the main band and evaporation
  5. customgave a gum
  6. customevaporated to dryness
  7. customre-evaporated with methanol

Sources & evidence

ORD record
ord-ea384129b02444a7b636d8bcb1fb179c
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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