2-Amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid → HCID 13118241, compound

HRID 1058520Notes

Reaction equation

HRID 1058520 reaction equation
N([O-])=[O:2].[Na+].[CH:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20](N)[C:21]([OH:23])=[O:22])=[O:14])=[CH:7][CH:6]=1>O.OS(O)(=O)=O.C(#N)C>[CH2:11]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([OH:2])[C:21]([OH:23])=[O:22])=[O:14])[C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 1025682-Amino-6-(((benzyloxy)carbonyl)amino)hexanoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 13118241HCID 13118241, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of NaNO2 in water (200 ml) was added dropwise during 3 hr to an ice-cooled and stirred solution of N-ε-CBZ-L-lysine in 1 N H2SO4 and acetonitrile. The mixture was stirred for an additional 2 hr after the addition of 0-5° C. and left to stand overnight. The resulting clear solution was concentrated under reduced pressure. The residual semi-solid was extracted with ether, and the ether extract was then crystallized in ether/petroleum ether. The products recovered was α-(N-CBZ-4-aminobutyl) glycolic acid.

Workup

  1. temperaturecooled
  2. additionafter the addition of 0-5° C.
  3. waitleft
  4. waitto stand overnight
  5. concentrationThe resulting clear solution was concentrated under reduced pressure
  6. extractionThe residual semi-solid was extracted with ether
  7. extractionthe ether extract
  8. customwas then crystallized in ether/petroleum ether
  9. customThe products recovered

Sources & evidence

ORD record
ord-a49520246241449688e43ef6b8a7db5f
Source dataset
uspto-grants-2003_02
Patent number
US06517869B1

Reaction notes

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