Ammonia → HCID 86665779, compound

HRID 2040736Notes

Reaction equation

HRID 2040736 reaction equation
[OH:1][CH:2]1[CH:6]([OH:7])[CH:5]([CH2:8][OH:9])[CH2:4][CH:3]1[N+:10]1[CH:15]=[CH:14][CH:13]=[C:12](C(OC)=O)[CH:11]=1.[CH3:20][S:21]([O-:24])(=[O:23])=[O:22].[NH3:25].[CH3:26][OH:27]>>[C:26]([C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[CH:3]1[CH2:4][CH:5]([CH2:8][OH:9])[CH:6]([OH:7])[CH:2]1[OH:1])(=[O:27])[NH2:25].[CH3:20][S:21]([O-:24])(=[O:23])=[O:22]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 50902485HCID 50902485, compound

Product 1

HCID 86665779HCID 86665779, compound

Procedure

Crude 1-(2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-3-methoxycarbonyl-pyridinium-methansulfonate (118.3 g, 173.7 mmol) was dissolved in 100.0 ml methanol. After the addition of methanolic ammonia (7M, 350.0 ml, 2.45 mol) the reaction mixture was stirred for 2.5 hrs. After removing the solvent under reduced pressure, a red-brown oil was obtained that was further dried for 3 hrs. (40° C., 10 mbar). This crude product may be pre-purified with activated charcoal and may be used directly for the chemical synthesis of cNAD (WO2007/012494) or in the enzymatic synthesis of cNAD as described herein.

Workup

  1. customAfter removing the solvent under reduced pressure
  2. customa red-brown oil was obtained
  3. customthat was further dried for 3 hrs
  4. custom(40° C., 10 mbar)
  5. customThis crude product may be pre-purified with activated charcoal
  6. custommay be used directly for the chemical synthesis of cNAD (WO2007/012494) or in the enzymatic synthesis of cNAD

Sources & evidence

ORD record
ord-111c2cdc031243bb864848a77b2ad12a
Source dataset
uspto-grants-2013_11
Patent number
US08580949B2

Reaction notes

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