Diisopropylethylamine → Fmoc-Lys(Mtr)-Lys(Mtr)

HRID 1883294Notes

Reaction equation

HRID 1883294 reaction equation
[NH:1]([C:32]([O:34][CH2:35][CH:36]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[C@H:2]([C:22](ON1C(=O)CCC1=O)=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:20]([CH3:21])=[C:18]([CH3:19])[C:15]([O:16][CH3:17])=[CH:14][C:12]=1[CH3:13])(=[O:10])=[O:9].[NH2:49][C@H:50]([C:70]([OH:72])=[O:71])[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][S:56]([C:59]1[C:68]([CH3:69])=[C:66]([CH3:67])[C:63]([O:64][CH3:65])=[CH:62][C:60]=1[CH3:61])(=[O:58])=[O:57].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[NH:1]([C:32]([O:34][CH2:35][CH:36]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])[C@H:2]([C:22]([NH:49][C@H:50]([C:70]([OH:72])=[O:71])[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][S:56]([C:59]1[C:68]([CH3:69])=[C:66]([CH3:67])[C:63]([O:64][CH3:65])=[CH:62][C:60]=1[CH3:61])(=[O:58])=[O:57])=[O:23])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[C:20]([CH3:21])=[C:18]([CH3:19])[C:15]([O:16][CH3:17])=[CH:14][C:12]=1[CH3:13])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 15662507Lys(Mtr)HCID 131724480Fmoc-Lys(Mtr)-OSu

Product 1

HCID 131724479Fmoc-Lys(Mtr)-Lys(Mtr)

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of Fmoc-Lys(Mtr)-OSu 3 (ca 8.672 mmol) and Lys(Mtr) 2 (3.6294 g, 1 equiv) in DMF (70 mL) at rt was treated with DIEA (4.5 mL, 3 equiv). After 4 h the mixture was diluted with ethyl acetate (250 mL). The solution was washed with pH 4 buffer (0.05M biphthalate) (2×), water and brine, dried over sodium sulfate and evaporated the residue was flushed with methylene chloride (400 mL) to give a pale-yellow foam which was carried on without further purification. 1H-NMR (CDCl3/CD3OD) δ 1.10-1.85 (m, 12H), 2.22 (m, 4H), 3.70 (m, 6H), 4.21 (m, 5H), 6.76 (m, 4H), 7.00-7.75 (m, 32H). MS (ESI) 1041. 6 (MH)+.

Workup

  1. washThe solution was washed with pH 4 buffer (0.05M biphthalate) (2×), water and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated the residue
  4. customwas flushed with methylene chloride (400 mL)
  5. customto give a pale-yellow foam which
  6. customwas carried on without further purification

Sources & evidence

ORD record
ord-f9d6eb33ec324560bd83c0d3fc8781ee
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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