Sodium Hydroxide → HCID 57001731, compound

HRID 843437Notes

Reaction equation

HRID 843437 reaction equation
C(OC([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[C@@H:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[O:46][CH3:47])=[CH:30][CH:29]=2)[C@H:10]([CH2:48][O:49][CH2:50][C@H:51]2[CH2:55][O:54]C(C)(C)[O:52]2)[CH2:9]1)=O)(C)(C)C.C(=O)([O-])O.[Na+].[OH-].[Na+]>CO.Cl.ClCCl>[CH3:47][O:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[CH2:39][O:38][CH2:37][CH2:36][CH2:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C@@H:11]2[C@@H:12]([O:14][CH2:15][C:16]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH2:13][NH:8][CH2:9][C@H:10]2[CH2:48][O:49][CH2:50][C@H:51]([OH:52])[CH2:55][OH:54])=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 57135722HCID 57135722, compound

Product 1

HCID 57001731HCID 57001731, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4.7 g (6 mmol) of (3S,4R,5R)-3-[(S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester in 50 ml of methanol and 44.4 ml of 2.7M hydrogenchloride in methanol was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was cooled to 0° C. and 20.1 g (239 mmol) of solid sodium hydrogencarbonate were added. Stirring was continued as long as carbondioxide was formed and the reaction mixture had reached room temperature. Then the mixture was adjusted to pH 8-9 by addition of 2 N sodium hydroxide solution and diluted with 250 ml of dichloromethane. The aqueous phase was separated and the organic phase dried over sodium sulfate and finally evaporated under reduced pressure. The residue which was thereby obtained was chromatographed on silica gel with a 90:10:0.1 mixture of dichloromethane, methanol and ammonium hydroxide as the eluent. There where thus obtained 2.7 g of (R)-3-[(3S,4R,5R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidin-3-ylmethoxy]-propane-1,2-diol in the form of an amorphous solid MS: 646 (M+H)+.

Workup

  1. customwas formed
  2. customhad reached room temperature
  3. customThe aqueous phase was separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. customfinally evaporated under reduced pressure
  6. customThe residue which was thereby obtained
  7. customwas chromatographed on silica gel with a 90:10:0.1 mixture of dichloromethane, methanol and ammonium hydroxide as the eluent

Sources & evidence

ORD record
ord-12942331c1ca4b57a3da0885464d02d3
Source dataset
uspto-grants-2002_04
Patent number
US06376672B1

Reaction notes

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