Diisopropylethylamine → Fmoc-Phe-Lys(MMT)

HRID 1767036Notes

Reaction equation

HRID 1767036 reaction equation
[NH:1]([C:20]([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[C@H:2]([C:10](ON1C(=O)CCC1=O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:37][C@H:38]([C:65]([OH:67])=[O:66])[CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:45]1[CH:52]=[CH:51][C:48]([O:49][CH3:50])=[CH:47][CH:46]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]([C:20]([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[C@H:2]([C:10]([NH:37][C@H:38]([C:65]([OH:67])=[O:66])[CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:45]1[CH:52]=[CH:51][C:48]([O:49][CH3:50])=[CH:47][CH:46]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10982650L-Lysine, N6-[(4-methoxyphenyl)diphenylmethyl]-HCID 11826988Fmoc-Phe-OSu

Product 1

HCID 131726498Fmoc-Phe-Lys(MMT)Yield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of Fmoc-Phe-OSu (2.0702 g, 4.2728 mmol, 1.0 eq) and Lys(MMT) (1.7995 g, 4.2995 mmol, 1.01 eq) in DMF (30 ml) was added DIEA (1.5 ml, 8.6112 mmol, 2.02 eq). The solid dissolved gradually and the solution was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate (100 ml) and pH5 buffer (0.05M phthalic acid, adjusted with 10N KOH to pH 5.0, 200 ml). The aqueous solution was extracted with more ethyl acetate (50 ml×2). The combined organic phase was washed with brine (50 ml×3), dried over MgSO4. After removal of solvent and being dried in vacuo, 3.3014 g (98.1%) of pale-yellow foam was obtained. ES(+)-MS: 516(M-MMT+1), 273(MMT).

Workup

  1. dissolutionThe solid dissolved gradually
  2. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and pH5 buffer (0.05M phthalic acid, adjusted with 10N KOH to pH 5.0, 200 ml)
  3. extractionThe aqueous solution was extracted with more ethyl acetate (50 ml×2)
  4. washThe combined organic phase was washed with brine (50 ml×3)
  5. dry with materialdried over MgSO4
  6. customAfter removal of solvent
  7. custombeing dried in vacuo

Sources & evidence

ORD record
ord-8d2bc539c87a41d480b8dd2feda164c3
Source dataset
uspto-grants-2007_06
Patent number
US07232805B2

Reaction notes

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