1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86678397, compound

HRID 882642Notes

Reaction equation

HRID 882642 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][N:7]([CH3:67])[C@H:8]([C:12]([NH:14][C@H:15]([C:19]([N:21]([C@@H:23]([C@@H:63]([CH3:66])[CH2:64][CH3:65])[C@H:24]([O:61][CH3:62])[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C@H:33]([O:59][CH3:60])[C@@H:34]([CH3:58])[C:35](=[O:57])[NH:36][C@H:37](/[CH:45]=[CH:46]/[C:47]1[CH:52]=[CH:51][C:50]([S:53]([OH:56])(=[O:55])=[O:54])=[CH:49][CH:48]=1)[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:27])[CH3:22])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH:9]([CH3:11])[CH3:10])([OH:3])=[O:2].O[N:69]1[C:73](=[O:74])[CH2:72][CH2:71][C:70]1=[O:75].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:75]=[C:70]1[CH2:71][CH2:72][C:73](=[O:74])[N:69]1[O:2][C:1](=[O:3])[CH2:4][CH2:5][CH2:6][N:7]([CH3:67])[C@H:8]([C:12]([NH:14][C@H:15]([C:19]([N:21]([C@@H:23]([C@@H:63]([CH3:66])[CH2:64][CH3:65])[C@H:24]([O:61][CH3:62])[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C@H:33]([O:59][CH3:60])[C@@H:34]([CH3:58])[C:35](=[O:57])[NH:36][C@H:37](/[CH:45]=[CH:46]/[C:47]1[CH:48]=[CH:49][C:50]([S:53]([OH:56])(=[O:55])=[O:54])=[CH:51][CH:52]=1)[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:27])[CH3:22])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH:9]([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 86678398HCID 86678398, compound

Product 1

HCID 86678397HCID 86678397, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8 mg (7.5 μmol) of N-(3-carboxypropyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(2S,3E)-1-phenyl-4-(4-sulphophenyl)but-3-en-2-yl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide in 2 ml of DMF were added 8.6 mg (74.8 μmol) of N-hydroxysuccinimide, 8.5 mg (22.4 μmol) of EDCI and 0.1 mg (0.75 μmol) of DMAP. The reaction mixture was stirred at RT for 20 h. Subsequently, 1.3 μl (7.5 μmol) of Hünig's base were added and the mixture was stirred for 1 h. The reaction mixture was then purified by prep. HPLC. 2.6 mg (72% purity, 21% of theory) of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customThe reaction mixture was then purified by prep

Sources & evidence

ORD record
ord-e73a7c04d1914027a0cc77df771716d5
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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