Ammonium Hydroxide → 3-Hydroxy-1-adamantyl-D-glycine

HRID 2060950Notes

Reaction equation

HRID 2060950 reaction equation
C([O-])=O.[NH4+:4].[OH:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([C:16](=O)[C:17]([OH:19])=[O:18])([CH2:9]3)[CH2:7]1)[CH2:13]2.[OH-].[NH4+]>C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.SC[C@H]([C@@H](CS)O)O>[NH2:4][C@@H:16]([C:8]12[CH2:14][CH:12]3[CH2:11][CH:10]([CH2:15][C:6]([OH:5])([CH2:13]3)[CH2:7]1)[CH2:9]2)[C:17]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723923Ammonium formateHCID 104661932-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid

Product 1

HCID 102630783-Hydroxy-1-adamantyl-D-glycineYield 105.5%

Reagents, catalysts & solvents 2

HCID 439153NadhCatalystHCID 446094D-1,4-DithiothreitolCatalyst

Procedure

A 266 ml solution was prepared containing ammonium formate (16.74 g, 0.2654 moles) and (3-hydroxy-adamantan-1-yl)-oxo-acetic acid (29.76 g, 0.1327 moles) and brought to pH 8.0 with 12.7 ml concentrated ammonium hydroxide. NAD (372 mg, 0.561 mmoles) and dithiothreitol (81.8 mg, 0.530 mmoles) were added, then the solution was added to the bottle containing the Escherichia coli extract. The bottle was maintained at 40° on a shaker at 40 rpm. Concentrated ammonium hydroxide was added periodically to maintain pH 8.0 After 38 hours, the solution contained 31.5 grams (0.140 moles, 100% yield) (S)-amino-(3-hydroxy-adamantan-1-yl)-acetic acid as measured by HPLC analysis and no R-enantiomer of the amino acid.

Workup

  1. additionthe solution was added to the bottle
  2. additioncontaining the Escherichia coli
  3. extractionextract
  4. temperatureThe bottle was maintained at 40° on a shaker at 40 rpm
  5. additionConcentrated ammonium hydroxide was added periodically
  6. temperatureto maintain pH 8.0 After 38 hours

Sources & evidence

ORD record
ord-209346a4803946dabfe13890c7824f14
Source dataset
uspto-grants-2012_10
Patent number
US08278462B2

Reaction notes

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