Diisopropyl Ether → N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-(triphenylmethyl)-L-glutamine 2,3,4,5,6-pentafluorophenyl ester

HRID 1110197Notes

Reaction equation

HRID 1110197 reaction equation
[NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OC(C)C)(C)C.[F:54][C:55]1[C:60](O)=[C:59]([F:62])[C:58]([F:63])=[C:57]([F:64])[C:56]=1[F:65].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([O:29][C:60]1[C:55]([F:54])=[C:56]([F:65])[C:57]([F:64])=[C:58]([F:63])[C:59]=1[F:62])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 10919157(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(triphenylmethyl)carbamoyl]butanoic acid

Product 1

HCID 11297250N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-(triphenylmethyl)-L-glutamine 2,3,4,5,6-pentafluorophenyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.5 g (2.27 mmol) of Fmoc-Gln(Trt)-OH×0.5 diisopropyl ether and 0.46 g (2.5 mmol) of pentafluoro-phenol are dissolved in 35 ml of ethyl acetate, cooled to 0° and, while stirring, 0.52 g (2.5 mmol) of dicyclohexylcarbodiimide is added. The mixture is stirred at 0° for 1 hour and at room temperature for 3 hours, and insoluble material is filtered off and washed with tetrahydrofuran. The filtrate is evaporated to dryness, and the residue is dissolved in 30 ml of tetrahydrofuran. Slow addition of petroleum ether while stirring results in crystallization of Fmoc-Gln(Trt)-OPfp; m.p. 185°-187°, [α]D20 =-16.4° (THF).

Workup

  1. temperaturecooled to 0°
  2. stirringThe mixture is stirred at 0° for 1 hour and at room temperature for 3 hours
  3. filtrationinsoluble material is filtered off
  4. washwashed with tetrahydrofuran
  5. customThe filtrate is evaporated to dryness
  6. dissolutionthe residue is dissolved in 30 ml of tetrahydrofuran
  7. additionaddition of petroleum ether
  8. stirringwhile stirring

Sources & evidence

ORD record
ord-b4cbe7779ee6426e84775aaa1ac41808
Source dataset
uspto-grants-1994_06
Patent number
US05324833

Reaction notes

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