Dicyclohexylcarbodiimide → HCID 131716001, compound

HRID 231939Notes

Reaction equation

HRID 231939 reaction equation
[CH:1]1([C:5]([NH:7][C@H:8]([C:24]([NH:26][CH:27]([P:35](=[O:38])([OH:37])[OH:36])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[O:6])[CH2:4][CH2:3][CH2:2]1.[C:39]1([CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][CH2:52][CH2:53][C@H:54](O)[C:55]([N:57]2[CH2:71][CH2:70][CH2:69][C@H:58]2[C:59]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[O:60])=[O:56])=[O:48])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:39]1([CH2:45][O:46][C:47]([NH:49][CH2:50][CH2:51][CH2:52][CH2:53][C@H:54]([O:38][P:35]([CH:27]([NH:26][C:24](=[O:25])[C@@H:8]([NH:7][C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([OH:37])=[O:36])[C:55]([N:57]2[CH2:71][CH2:70][CH2:69][C@H:58]2[C:59]([O:61][CH2:62][C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)=[O:60])=[O:56])=[O:48])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13934652HCID 13934652, compoundHCID 54308607HCID 54308607, compound

Product 1

HCID 131716001HCID 131716001, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

[1-[[N2 -(Cyclobutylcarbonyl)-N6 -[(phenylmethoxy) carbonyl]-L-lysyl]amino]-2-phenylethyl]phosphonic acid (500 mg., 0.91 mmole) is dissolved in pyridine (10 ml.) with 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-hydroxy-1-oxohexyl]-L-proline, phenylmethyl ester (426 mg., 0.91 mmole). Dicyclohexylcarbodiimide (224 mg., 1.09 mmole) is added and the mixture is stirred at room temperature overnight. It is then concentrated in vacuo and partitioned between ethyl acetate and 5% potassium bisulfate after filtering to remove dicyclohexyl urea. The ethyl acetate layer is washed with brine, dried over sodium sulfate, and concentrated to give 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-[[[1-[[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-[(cyclobutylcarbonyl)amino]-1-oxohexyl]amino]-2-phenylethyl]hydroxyphosphinyl]oxy]-1-oxohexyl]-L-proline, phenylmethyl ester as a crude oil. TLC (silica gel; dichloromethane:methanol:acetic acid, 20:1:1) Rf =0.33.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. custompartitioned between ethyl acetate and 5% potassium bisulfate
  3. filtrationafter filtering
  4. customto remove dicyclohexyl urea
  5. washThe ethyl acetate layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-162487d97cae4106b1ea8744a9ae66d6
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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