6-Aminohexanoic Acid → HCID 178525441, compound

HRID 1195153Notes

Reaction equation

HRID 1195153 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-87867f9b14454a9da61a1ce9d148b12e
Source dataset
uspto-grants-1992_05
Patent number
US05110812

Reaction notes

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