HCID 13338812, compound → HCID 19908727, compound

HRID 1534983Notes

Reaction equation

HRID 1534983 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][CH:16]1[CH:21]([OH:22])[CH2:20][CH2:19][CH2:18][CH:17]1[OH:23])=[O:14])=O)C1C=CC=CC=1>C(O)C.Cl>[OH:22][CH:21]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:23])[CH:16]1[NH:15][C:13](=[O:14])[CH2:12][NH2:11]

Participants

4

Reactant 1

HCID 13338812HCID 13338812, compound

Product 1

HCID 19908727HCID 19908727, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

N-protected benzyloxycarbonyl N-(2,6-dihydroxycyclohexyl) glycinamide (3 g, 0.093 mol) was dissolved in 100 ml of absolute ethanol with a molar equivalent of 10% HCl. Hydrogenolysis with 5% Pd/C at 30 psi, removal of the catalyst over celite, and subsequent evaporation of solvents in vacuo yielded a pale brownish solid which was triturated with ether and recrystallized from ethyl acetate and ether, m.p. 207°-210° C. NMR (D2O) δ, 3.65 (t, 3H, C1H of cyclohexane ring); 3.55 (m, 2H, C2H and C6H of cyclohexane); 3.4 (s, 2H, --CO--CH2 --NH2); 2.05, 1.80, and 1.38 (m,m,m, 2 to 1 to 3H, hydrogens of C3, C4 and C5 of cyclohexane).

Workup

  1. customHydrogenolysis with 5% Pd/C at 30 psi, removal of the catalyst
  2. customover celite, and subsequent evaporation of solvents in vacuo
  3. customyielded a pale brownish solid which
  4. customwas triturated with ether
  5. customrecrystallized from ethyl acetate and ether, m.p. 207°-210° C

Sources & evidence

ORD record
ord-ed81541f36d24a60b8c98d9528cb19ea
Source dataset
uspto-grants-1992_02
Patent number
US05091523

Reaction notes

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