Triethylamine → HCID 178462025, compound

HRID 1252522Notes

Reaction equation

HRID 1252522 reaction equation
[NH2:1][CH:2]([CH:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1)[CH3:7])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH2:26]([O:33][C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][C@H:41]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:42](O)=[O:43])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.O1CCOCC1>[CH2:26]([O:33][C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][C@H:41]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:42]([NH:1][C@@H:2]([C@H:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1)[CH3:7])[C:3]([OH:5])=[O:4])=[O:43])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724765Boc-Lys(Z)-OHHCID 178464544HCID 178464544, compound

Product 1

HCID 178462025HCID 178462025, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2S,3R)-2-amino-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (400 mg) and triethylamine (0.70 ml) in a mixture of water (10 ml) and dioxane (10 ml) was added (2S)-6-benzyloxycarbonylamino-2-t-butoxycarbonylaminohexanoic acid (894 mg) at 5° C. and the mixture was stirred in an ice-bath for 3 hours. The volatile solvent was evaporated in vacuo and the residue was adjusted to pH 4 with 1N hydrochloric acid. The mixture was subjected to a column of "Diaion HP-20" (80 ml). After the column was washed with water, the elution was carried out with a mixture of methanol and water (3:7-8:2) and the object fractions were collected and evaporated in vacuo. The residue was solidified with a mixture of methanol and ether to give (2S,3R)-2-[[(2S)-6-benzyloxycarbonylamino-2-t-butoxycarbonylaminohexanoyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]butyric acid (786 mg) as a white powder.

Workup

  1. customThe volatile solvent was evaporated in vacuo
  2. washAfter the column was washed with water
  3. washthe elution
  4. additionwas carried out with a mixture of methanol and water (3:7-8:2)
  5. customthe object fractions were collected
  6. customevaporated in vacuo
  7. additionThe residue was solidified with a mixture of methanol and ether

Sources & evidence

ORD record
ord-324cf42b3853436ea497a60d50c8366b
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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