N-Hydroxysuccinimide → HCID 86678373, compound

HRID 882618Notes

Reaction equation

HRID 882618 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:70])[C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:66]([CH3:69])[CH2:67][CH3:68])[C@H:26]([O:64][CH3:65])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:62][CH3:63])[C@@H:36]([CH3:61])[C:37]([NH:39][C@@H:40]([CH2:51][C:52]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[NH:54][CH:53]=1)[C:41]([NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH:11]([CH3:13])[CH3:12])([OH:3])=[O:2].O[N:72]1[C:76](=[O:77])[CH2:75][CH2:74][C:73]1=[O:78].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C1C=CN=CC=1)C>[O:78]=[C:73]1[CH2:74][CH2:75][C:76](=[O:77])[N:72]1[O:2][C:1](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:70])[C@H:10]([C:14]([NH:16][C@H:17]([C:21]([N:23]([C@@H:25]([C@@H:66]([CH3:69])[CH2:67][CH3:68])[C@H:26]([O:64][CH3:65])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C@H:35]([O:62][CH3:63])[C@@H:36]([CH3:61])[C:37]([NH:39][C@@H:40]([CH2:51][C:52]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[NH:54][CH:53]=1)[C:41]([NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])=[O:38])=[O:29])[CH3:24])=[O:22])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56952892HCID 56952892, compound2×

Product 1

HCID 86678373HCID 86678373, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

17 mg (18 μmol) of N-(5-carboxypentyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-(benzylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Intermediate 98) were dissolved in 2.8 ml of dichloromethane and admixed with 20 mg (174 mmol) of 1-hydroxypyrrolidine-2,5-dione and then with 10 mg (52 μmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.21 mg (0.17 μmol) of DMAP. After stirring at RT for 4 h, the reaction mixture was concentrated under reduced pressure. The remaining residue was purified by means of preparative HPLC. After lyophilization, 8.2 mg (43% of theory) of the title compound were obtained.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe remaining residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-ad62eabad7894f34af8454017bb64310
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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