Urea → HCID 67982992, compound

HRID 928709Notes

Reaction equation

O1C=CC=C1.[NH:6]([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12].C(N)(N)=O.[CH2:37]([N:43]=[C:44]=[O:45])[C:38]1[O:42][CH:41]=[CH:40][CH:39]=1>>[CH:22]1[C:21]2[CH:20]([CH2:19][O:18][C:16]([NH:6][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:44]([NH:43][CH2:37][C:38]3[O:42][CH:41]=[CH:40][CH:39]=3)=[O:45])[C:13]([OH:15])=[O:14])=[O:17])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

Reactant 4

HCID 1176Urea

HCID 8029Furan

HCID 42238112-(Isocyanatomethyl)furan

HCID 7010557(2S)-6-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

Product 1

HCID 67982992HCID 67982992, compound

Procedure

After Boc deprotection of the Fmoc-Lys(Boc)-OH, Fmoc-Lys-OH was obtained (FIG. 23, (1)). The furan moiety was coupled to the ε-amine of Fmoc-Lys-OH by ureum formation with furfuryl isocyanate to obtain 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(3-(furan-2-ylmethyl)ureido)hexanoic acid (FIG. 23, (2)), or by amide formation with pentafluorophenyl-furan-2-carboxylate (FIG. 23, (4)) to obtain 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(furan-2-carboxamido)hexanoic acid (FIG. 23, (5)). The synthesis was finished with Fmoc deprotection, yielding the amphiphilic products (3) or (6) (FIG. 23) as a white powder. Hence, the furan amino acid of Formula (XId) or the furan amino acid of Formula (XIc) was obtained (FIG. 23, (3) or (6) respectively).

Sources & evidence

ORD record: ord-a6cfbaa9a8974c4db4b292ed85922363
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290537B2

Reaction notes

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