2H-Azepin-2-one, hexahydro-1-(hydroxymethyl)- → HCID 22628914, compound

HRID 277343Notes

Reaction equation

HRID 277343 reaction equation
[CH2:1]([CH:8]1[C:31](=[O:32])[N:30]([CH3:33])[CH:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:28](=[O:38])[O:27][CH:26]([CH3:39])[CH2:25][N:24]([CH3:40])[CH:23]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:22](=[O:45])[O:21][CH:20]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:19](=[O:53])[N:18]([CH3:54])[CH:17]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:16](=[O:59])[O:15][CH:14]([CH3:60])[CH2:13][N:12]([CH3:61])[CH:11]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:10](=[O:66])[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:68][N:69]1[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71][C:70]1=[O:76].C(=O)(O)[O-].[Na+]>FC(F)(F)S(O)(=O)=O>[CH2:46]([CH:20]1[C:19](=[O:53])[N:18]([CH3:54])[CH:17]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:16](=[O:59])[O:15][CH:14]([CH3:60])[CH2:13][N:12]([CH3:61])[CH:11]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:10](=[O:66])[O:9][CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:68][N:69]3[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71][C:70]3=[O:76])=[CH:6][CH:7]=2)[C:31](=[O:32])[N:30]([CH3:33])[CH:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:28](=[O:38])[O:27][CH:26]([CH3:39])[CH2:25][N:24]([CH3:40])[CH:23]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:22](=[O:45])[O:21]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 831272H-Azepin-2-one, hexahydro-1-(hydroxymethyl)-HCID 516892Sodium BicarbonateHCID 22628884HCID 22628884, compound

Product 1

HCID 22628914HCID 22628914, compound

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

At 0° C., 200 ml of trifluoromethanesulfonic acid were initially charged and 20 g (0.0217 mol) of 8,20-dibenzyl-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone (1-b) (for example from Ex. 1) and 6.2 g (0.0434 mmol) of N-hydroxymethyl-ε-caprolactam were added successively, and the mixture was stirred at room temperature for 20 h. The mixture was then poured onto ice, neutralized by addition of solid sodium bicarbonate and subsequently extracted with dichloromethane. The combined extracts were washed with little water, dried and concentrated. The resulting 26 g of crude product were separated by MPLC. The first main fraction gave 1.22 g of singly amidoalkylated compound 20-benzyl-8-[4-(2-oxoazepan-1-ylmethyl)benzyl]-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone (20-a). After intermediate fractions of a total of 4.21 g, 5.59 g of doubly amidoalkylated compound 8.20-bis-[4-(2-oxoazepan-1-ylmethyl)benzyl]-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone (20-b) were obtained.

Workup

  1. additionThe mixture was then poured onto ice
  2. extractionsubsequently extracted with dichloromethane
  3. washThe combined extracts were washed with little water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting 26 g of crude product were separated by MPLC

Sources & evidence

ORD record
ord-ffb24838f2684e44950639637c6f313f
Source dataset
uspto-grants-2002_03
Patent number
US06355615B1

Reaction notes

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