Triethylamine → HCID 12944618, compound

HRID 649088Notes

Reaction equation

HRID 649088 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:6]([O:8]N1C(=O)CCC1=O)=O)[CH:3]([CH3:5])[CH3:4].[NH2:23][C@H:24]([C:40]([O:42][CH3:43])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].Cl.C(N(CC)CC)C>C1COCC1>[NH:1]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:2]([C:6]([NH:23][C@H:24]([C:40]([O:42][CH3:43])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98768Boc-Val-osuHCID 1293537127894-50-4

Product 1

HCID 12944618HCID 12944618, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of t-Boc-Val-OSu (3.14 g, 10 mmol) and H-Lys(CBZ)-OCH3.HCl (3.31 g, 10 mmol) in THF (300 ml) was treated at room temperature with triethylamine (1.38 ml) and left stirring for 17 hr. The resulting solution was evaporated in vacuo and the residue was dissolved in EtOAc (500 ml). The organic solution was washed successively with water (2×200 ml), 5% citric acid (2×200 ml), water (2×200 ml) and dried over Na2SO4. The dried solution was filtered and evaporated in vacuo to give (VI) (4.9 g; 99%) as a foam. T.l.c. RfE4 =0.64.

Workup

  1. waitleft
  2. customThe resulting solution was evaporated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (500 ml)
  4. washThe organic solution was washed successively with water (2×200 ml), 5% citric acid (2×200 ml), water (2×200 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationThe dried solution was filtered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-41cf3b78fcb148b582cc1f92fa0a07a1
Source dataset
uspto-grants-1988_04
Patent number
US04737487

Reaction notes

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