HCID 22289804, compound → HCID 87663615, compound

HRID 2112568Notes

Reaction equation

HRID 2112568 reaction equation
Cl.Cl.Cl.Cl.[NH2:5][CH2:6][CH2:7][CH2:8][S:9][CH2:10][CH2:11][O:12][C@@H:13]1[C@@H:21]([O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][NH2:29])[C@@H:20]([O:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][CH2:36][NH2:37])[C@@H:19]([CH2:38][O:39][CH2:40][CH2:41][S:42][CH2:43][CH2:44][CH2:45][NH2:46])[O:18][C@@H:14]1[O:15][CH2:16][CH3:17].COC([C:51]1[C:52](N[C:55](=[O:57])[CH:56]=1)=[O:53])=O>C([O-])(O)=O.[Na+].O.C(#N)C.C(Cl)Cl>[C:19]1(=[O:18])[N:5]([CH2:6][CH2:7][CH2:8][S:9][CH2:10][CH2:11][O:12][C@@H:13]2[C@@H:21]([O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][N:29]3[C:52](=[O:53])[CH:51]=[CH:56][C:55]3=[O:57])[C@@H:20]([O:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][CH2:36][N:37]3[C:52](=[O:53])[CH:51]=[CH:56][C:55]3=[O:57])[C@@H:19]([CH2:38][O:39][CH2:40][CH2:41][S:42][CH2:43][CH2:44][CH2:45][N:46]3[C:52](=[O:53])[CH:51]=[CH:56][C:55]3=[O:57])[O:18][C@@H:14]2[O:15][CH2:16][CH3:17])[C:13](=[O:12])[CH:21]=[CH:20]1

Participants

7

Reactant 2

HCID 22289804HCID 22289804, compoundHCID 69029414HCID 69029414, compound

Product 1

HCID 87663615HCID 87663615, compoundYield 351%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of amine 8 (23.9 mg, 29.0 μmol) dissolved in 1 M aqueous solution of NaHCO3 (1 mL) was treated with methoxycarbonylmaleimide (27.03 mg, 17.4 μmol) at 0° C. After 5 min, the mixture was diluted with water (1 mL) and acetonitrile (2 mL), and then stirred at room temperature for 1 h. The mixture was diluted with CH2Cl2 (50 mL) and washed with brine (3×10 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The oily residue was purified by flash chromatography (CH2Cl2/MeOH 96:4) to give maleimide 9 (20.3 mg, 71%); Rf 0.45 (CH2Cl2/MeOH 96:4); 1H-NMR (CDCl3/TMS): δ6.72 (s, 8H, CH═CH), 4.94 (d, 1H, J=3.4 Hz, H-1), 3.95-3.82 (m, 2H, H-4, and OCHHCH2CH2N), 3.80˜3.45 (m, 22H, H-2, H-3, H-5, H-6, H-6′, OCH2CH2CH2S, SCH2CH2N, and OCH2CH3), 2.90-2.60 (m, 16H, OCH2CH2CH2SCH2CH2N), 1.96-1.82 (m, 8H, OCH2CH2CH2S), 1.23 (t, 3H, J=7.1 Hz, OCH2CH3); ES-MS: 1019.49 (M+Na)+, 951(M-OEt)+.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was purified by flash chromatography (CH2Cl2/MeOH 96:4)

Sources & evidence

ORD record
ord-507dbea6bb03423ca88bfbd1c76d0764
Source dataset
uspto-grants-2009_04
Patent number
US07524821B2

Reaction notes

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