Hydrochloric Acid → HCID 70276607, compound

HRID 2287656Notes

Reaction equation

HRID 2287656 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O-:11])=[O:10].[Na+].Cl.[NH:14]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:15]([C:23](ON1C(=O)CCC1=O)=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(=O)(=O)(O)O>O1CCOCC1>[C:36]([O:35][C:33]([NH:14][C@H:15]([C:23]([CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[C:9]([OH:11])=[O:10])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:34])([CH3:38])([CH3:39])[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 107447tert-Butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 23665043HCID 23665043, compound

Product 1

HCID 70276607HCID 70276607, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 250 mL round bottom flask equipped with an addition funnel was added a solution of sodium 8-aminocaprylate (14.61 mmol, 32.5 mL, 1.2 equiv). The pH of the solution was adjusted to 8.2 by addition of concentrated HCl. The solution was cooled in an ice-bath. Boc-Phe-OSu (12.42 mmol, 4.50 g, 1.0 equiv) was dissolved in 1,4-dioxane (20 mL) and added dropwise. The mixture was stirred in the ice-bath for 30 min and at ambient temperature for 12 h. The solution was acidified with 1 M sulfuric acid (80 mL) and extracted with ether (100+50 mL). The combined organic layers were washed with water (40 mL), dried and evaporated to give a pale yellow oil. The oil was triturated with hexanes (3×50 mL) to afford (N-tert-butoxycarbonylphenylalanyl)-8-aminocaprylic acid (5) (2.17 g, 43%) as a colorless solid.

Workup

  1. customTo a 250 mL round bottom flask equipped with an addition funnel
  2. temperatureThe solution was cooled in an ice-bath
  3. additionadded dropwise
  4. extractionextracted with ether (100+50 mL)
  5. washThe combined organic layers were washed with water (40 mL)
  6. customdried
  7. customevaporated
  8. customto give a pale yellow oil
  9. customThe oil was triturated with hexanes (3×50 mL)

Sources & evidence

ORD record
ord-cdcf4670181047718d64d9c2566163e4
Source dataset
uspto-grants-2000_07
Patent number
US06084112

Reaction notes

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