Methanol → 2-Aminohexadecanoic acid

HRID 1604131Notes

Reaction equation

HRID 1604131 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C(N[C@H](C(O)=O)CCCCN)(O[CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=O.C([N:37](CC)CC)C.CO.C(Cl)Cl.CO>C(Cl)Cl>[NH2:37][CH:2]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 21226129Dichloromethane methanolHCID 69015819HCID 69015819, compound

Product 1

HCID 4093222-Aminohexadecanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

830 mg (1.53 mmole) of the N-hydroxysuccinimide ester of 3β-(2'-carboxymethoxycholest-5-ene) obtained as previously described (Ahmad et al. J. Chem., 24, 143-151) was added to a solution of 746 mg (1.53 mmoles) of Nα-Fmoc-lysine trifluoroacetate (obtained by trifluoroacetic acid deprotection of Nα-Fmoc-NεBoc-lysine), and 0.214 ml of triethylamine in 5 ml of methylene chloride. The reaction mixture was stirred overnight at room temperature. After addition of methanol (5 ml), and methylene chloride (20 ml), the reaction mixture was washed with 10-2 aqueous HCl. The organic layer was dried, and evaporated to give crystals. Yield: 0.88 g (73%). m.p.=89° C. Rf=0.5 (methylene chloride/methanol, 9/1), m/z: 795 [M+H]+.

Workup

  1. washthe reaction mixture was washed with 10-2 aqueous HCl
  2. customThe organic layer was dried
  3. customevaporated
  4. customto give crystals

Sources & evidence

ORD record
ord-7a095fa3c4594f6cb920e2bff99cdd2e
Source dataset
uspto-grants-1999_11
Patent number
US05993823

Reaction notes

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