HCID 69406722, compound → HCID 10174650, compound

HRID 916816Notes

Reaction equation

HRID 916816 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:54])[CH2:13][NH:14][CH2:15][CH2:16][C:17]3[CH:53]=[CH:52][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:27]=[C:28]([S:32]([N:35](COCC[Si](C)(C)C)COCC[Si](C)(C)C)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=4)=[CH:19][CH:18]=3)=[CH:11][C:5]=2[CH2:4][O:3]1>C(O)(=O)C.O>[OH:54][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][C:17]1[CH:53]=[CH:52][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]2[CH:27]=[C:28]([S:32]([NH2:35])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 69406722HCID 69406722, compound

Product 1

HCID 10174650HCID 10174650, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-({2-[4-(2-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}ethyl)phenoxy]ethoxy}methyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (0.015 g) was heated at 75° for 6 h in acetic acid (1.5 ml) and water (0.75 ml). The solution was evaporated to dryness and re-evaporated twice with methanol to give crude product (0.012 g). This was purified by preparative layer chromatography on a silica plate (20×20 cm) which was developed twice in dichloromethane:ethanol: 0.880 ammonia solution, 25:8:1. After elution of the required band using methanol in dichloromethane, the eluate was evaporated to dryness and re-evaporated successively with acetic acid in methanol and then methanol to give the title compound (0.0037 g) LCMS RT=2.19 min. ES+ve 517 (MH)+

Workup

  1. customThe solution was evaporated to dryness
  2. customre-evaporated twice with methanol
  3. customto give crude product (0.012 g)
  4. customThis was purified by preparative layer chromatography on a silica plate (20×20 cm) which
  5. washAfter elution of the required band
  6. customthe eluate was evaporated to dryness
  7. customre-evaporated successively with acetic acid in methanol

Sources & evidence

ORD record
ord-68105506f8bf48fd841eeac634aa50de
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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