N-Hydroxysuccinimide → HCID 22816298, compound

HRID 1680208Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C@H:6]([C:18]([OH:20])=[O:19])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[O:4].O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30]>>[F:1][C:2]([F:21])([F:22])[C:3]([NH:5][C@H:6]([C:18]([O:20][CH:26]1[CH2:27][C:28](=[O:29])[NH:24][C:25]1=[O:30])=[O:19])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:15])([F:16])[F:14])=[O:4]

Participants

Reactant 2

HCID 80170N-Hydroxysuccinimide

HCID 14251841329-53-3

Product 1

HCID 22816298HCID 22816298, compound

Procedure

N,N'-bis-trifluoroacetyl-L-lysine is treated with N-hydroxysuccinimide according to Example 2A to obtain N,N'-bis-trifluoroacetyl-L-lysyloxy succinimide; [α]D26 -31.4° (EtOH); νmax (KBr) 1810, 1790, 1740, 1700 cm-1. This product (473 mg) is added under nitrogen to amphotericin B (500 mg) in 5 ml of a 9:1 dimethylsulfoxide:methanol mixture. After 3.5 hours, 6 ml of methanol is added and the mixture is added dropwise to excess ether. A fine, yellow precipitate is allowed to settle with cooling overnight. Filtration, washing with ether and drying gives the named compound: [α]D26 +263.2 (dimethylsulfoxide); νmax (KBr) 1710 cm-1.

Sources & evidence

ORD record: ord-2db47b9d2a6144d2a964face100b6fed
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04272525

Reaction notes

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