6-Aminohexanoic Acid → HCID 178525441, compound

HRID 1682124Notes

Reaction equation

HRID 1682124 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-4c61569902254f628361d0b80b781c70
Source dataset
uspto-grants-1992_12
Patent number
US05175283

Reaction notes

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