Benzene → N-Fmoc-L-isoleucine

HRID 1047399Notes

Reaction equation

[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:14][C@H:15]([C:20]([OH:22])=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17].N[C@H]([C:26]([OH:28])=[O:27])C.[CH:29]1C=CC=CC=1>>[NH:14]([C:26]([O:28][CH2:29][CH:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:27])[C@H:15]([C:20]([OH:22])=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17]

Participants

Reactant 4

HCID 241Benzene3×

HCID 5950L-Alanine3×

HCID 6306L-Isoleucine3×

HCID 6853Fluorene

Product 1

HCID 2724629N-Fmoc-L-isoleucine

Procedure

0.88 (3H, t, J=6.9, —OC17H34-Me) 1.20-2.20 (75H, br, m, Alkyl-H, Ile Me-CH2—CH-Me, Pro N—CH2CH2—CH2—CH, Ala Me) 2.30 (1H, br, s, Ile Me-CH2—CH-Me) 3.38 (4H, t, J=6.6, —CH2—O—CH2—C21H43) 3.58 (1H, br, Pro CO—N—CH2—) 3.70 (1H, br, Pro CO—N—CH2—) 3.88 (2H, br, t, J=6.6, fl-O—CH2—) 4.19 (1H, t, J=6.6, fluorene (Fmoc) C9-H) 4.25-4.45 (3H, m, fluorene (Fmoc)-CH2—O, Ile or Pro or Ala α-H) 4.50 (1H, br, m, Ile or Pro or Ala α-H) 4.66 (1H, br, m, Ile or Pro or Ala α-H) 5.40 (1H, d, J=9.3, Fmoc-NH—) 6.75-7.45 (12H, m, fluorene-H or Ph-H) 7.57 (4H, br, fluorene-H or Ph-H) 7.75 (2H, d, J=7.8, fluorene-H or Ph-H)

Sources & evidence

ORD record: ord-f391b1ed173e4db4bc256859cfc35637
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569453B2

Reaction notes

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