Diisopropylethylamine → HCID 117995797, compound

HRID 1488297Notes

Reaction equation

HRID 1488297 reaction equation
[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:58])[CH2:16][N:17]([CH2:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:45])=[O:37])[CH2:18][C:19](=[O:34])[NH:20][CH2:21][CH2:22][O:23][C@@H:24]2[O:32][C@@H:31]([CH3:33])[C@@H:29]([OH:30])[C@@H:27]([OH:28])[C@@H:25]2[OH:26])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].Cl.[NH2:60][CH2:61][C@@H:62]([C:81]([OH:83])=[O:82])[NH:63][C:64]([O:66][CH2:67][CH:68]1[C:80]2[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=2[C:74]2[C:69]1=[CH:70][CH:71]=[CH:72][CH:73]=2)=[O:65].CCN(C(C)C)C(C)C>CN(C=O)C>[O:58]=[C:15]([NH:14][CH2:13][CH2:12][O:11][C@@H:1]1[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3])[CH2:16][N:17]([CH2:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([NH:60][CH2:61][C@@H:62]([C:81]([OH:83])=[O:82])[NH:63][C:64]([O:66][CH2:67][CH:68]1[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][C:74]=2[C:75]2[C:80]1=[CH:79][CH:78]=[CH:77][CH:76]=2)=[O:65])=[O:45])=[O:37])[CH2:18][C:19]([NH:20][CH2:21][CH2:22][O:23][C@@H:24]1[O:32][C@@H:31]([CH3:33])[C@@H:29]([OH:30])[C@@H:27]([OH:28])[C@@H:25]1[OH:26])=[O:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 49853440HCID 49853440, compoundHCID 117995923HCID 117995923, compound

Product 1

HCID 117995797HCID 117995797, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of pentafluorophenyl 6-[({bis[2-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}acetyl)amino]hexanoate (270 mg, 0.318 mmol) in DMF at 0° C. was added 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine hydrochloride (303 mg, 0.306 mmol) and, 5 min later, DIPEA (111 μL, 0.636 mmol). After stirring at 0° C. for 2 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (22 g), eluting first with 100 mL of EtOAc and then 0-20% of Solvent B in Solvent A (Solvent A: v/v EtOAc/MeOH/AcCN/H2O: 6/1/1/1; Solvent B v/v EtOAc/MeOH/AcCN/H2O: 2/1/1/1) to afford the title compound. LC-MS Method A: m/e=991.66 [M+1]; Rt=1.84 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (22 g)
  3. washeluting first with 100 mL of EtOAc

Sources & evidence

ORD record
ord-c4ee1b5c249b4f26a5dbf742f61f6ec8
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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