6-Aminohexanoic Acid → HCID 178525441, compound

HRID 1728491Notes

Reaction equation

HRID 1728491 reaction equation
[C:1]([NH:11][C:12](=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])SC)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.[NH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40]>>[C:16]([N:15]=[C:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

4

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 8471TriethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothiourea

Product 1

HCID 178525441HCID 178525441, compoundYield 66%

Procedure

A methanolic (350 mL) solution of N, N'-dicarbobenzyloxy-S-methyl-isothiourea (60 g, 0.18 mol), triethylamine(18.2 g, 0.18 mol), and 6-aminocaproic acid (23.3 g, 0.18 mol) was refluxed for 30 min and subsequently stirred at room temperature for 4 h. The solution was concentrated, and the residue was partitioned between ethyl acetate and water. The organic phase was separated, dried (MgSO4), and concentrated. The residual solid was recrystallized from ethyl acetate/hexane to afford 52.3 g (66%) of the title product, mp 93° C.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residual solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-fe98c531a95f49ce88edbe7afb2566ac
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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