Acetic Acid → HCID 58458959, compound

HRID 2387764Notes

Reaction equation

HRID 2387764 reaction equation
[C:1]([C:3]1([NH:9][C:10]([O:12][C@@H:13]([CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])=[O:11])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].C=O.[C:31](O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([C:3]1([NH:9][C:10]([O:12][C@@H:13]([CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])=[O:11])[CH2:8][CH2:7][N:6]([CH3:31])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67300943HCID 67300943, compound

Product 1

HCID 58458959HCID 58458959, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A sample of the free amine obtained from the previous step (40 mg, 0.102 mmol) is dissolved in MeOH (1 mL) and formaldehyde (6.06 mg, 0.202 mmol) is added as a solution in methanol (2 mL) with a single drop of acetic acid. Sodium cyanoborohydride (2.1 mg, 0.034 mmol) is added as a solid and the reaction is allowed to stir for half an hour. The solvent is removed in vacuo and the product is purified by preparative HPLC to afford the title material, 29.8 mg, 72% yield. HPLC-MS calculated for C21H34N4O4 (M+H+)407.3, found 407.3.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-5f786cd277d54c278ca03cc9e53d0bd3
Source dataset
uspto-grants-2012_09
Patent number
US08268996B2

Reaction notes

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