Diisopropylethylamine → 9H-fluoren-9-ylmethyl N-(1-{[4-({2-[2-(2-{[(tertbutoxy)carbonyl]amino}ethoxy)ethoxy]ethyl}carbamoyl)phenyl]methyl}piperidin-4-yl)carbamate

HRID 535909Notes

Reaction equation

HRID 535909 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=4)[CH2:21][CH2:20]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][CH2:74][NH:75][C:76](=[O:82])[O:77][C:78]([CH3:81])([CH3:80])[CH3:79]>CN(C=O)C>[C:78]([O:77][C:76]([NH:75][CH2:74][CH2:73][O:72][CH2:71][CH2:70][O:69][CH2:68][CH2:67][NH:66][C:30]([C:29]1[CH:33]=[CH:34][C:26]([CH2:25][N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]3[C:13]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:20][CH2:21]2)=[CH:27][CH:28]=1)=[O:31])=[O:82])([CH3:79])([CH3:81])[CH3:80]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9881394tert-butyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamateHCID 866878634-[(4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidin-1-yl)methyl]benzoic acid

Product 1

HCID 866878629H-fluoren-9-ylmethyl N-(1-{[4-({2-[2-(2-{[(tertbutoxy)carbonyl]amino}ethoxy)ethoxy]ethyl}carbamoyl)phenyl]methyl}piperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[(4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidin-1-yl)methyl]benzoic acid (1.20 g; 2.63 mmol), TBTU (1.01 g; 3.15 mmol) and DIPEA (1.8 ml; 3.15 mmol) in DMF (10 ml) is stirred for 5 min. tert-Butyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (783 mg; 3.15 mmol) is added and the mixture is stirred overnight. Volatiles are evaporated and the product is purified by RP-HPLC (modifier: TFA) to yield 9H-fluoren-9-ylmethyl N-(1-{[4-({2-[2-(2-{[(tertbutoxy)carbonyl]amino}ethoxy)ethoxy]ethyl}carbamoyl)phenyl]methyl}piperidin-4-yl)carbamate.

Workup

  1. additionis added
  2. customVolatiles are evaporated
  3. customthe product is purified by RP-HPLC (modifier: TFA)

Sources & evidence

ORD record
ord-8c45fd83676d49f885d204e52fc42dcd
Source dataset
uspto-grants-2014_10
Patent number
US08859559B2

Reaction notes

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