Hydrochloric Acid → HCID 136387743, compound

HRID 1924382Notes

Reaction equation

HRID 1924382 reaction equation
[I:1][C:2]1[C:3]2[C:27]3=[CH:28][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]4[O:38][C:15]([NH:16][C@@H:17]([CH:35]([CH3:37])[CH3:36])[C:18](=[O:34])[N:19]5[CH2:29][C@H:22]([O:23][C:24]3=[N:25][CH:26]=1)[CH2:21][C@H:20]5[C:30]([O:32]C)=[O:31])=[N:14][N:13]=4)=[CH:5][CH:4]=2.[Li+].[OH-].Cl>C1COCC1.O>[I:1][C:2]1[C:3]2[C:27]3=[CH:28][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]4[O:38][C:15]([NH:16][C@@H:17]([CH:35]([CH3:36])[CH3:37])[C:18](=[O:34])[N:19]5[CH2:29][C@H:22]([O:23][C:24]3=[N:25][CH:26]=1)[CH2:21][C@H:20]5[C:30]([OH:32])=[O:31])=[N:14][N:13]=4)=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 136387741HCID 136387741, compound

Product 1

HCID 136387743HCID 136387743, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl (3R,5S,8S)-23-iodo-8-isopropyl-7-oxo-2,28-dioxa-6,9,11,12,25-pentaazapentacyclo[17.6.2.13,6.110,13.022,26]noncosa-1(25),10,12,19,21,23,26-heptaene-5-carboxylate (from Step 2) in THF/H2O (1/1 v/v) was added LiOH (4 eq). The resulting reaction mixture was stirred at RT for 2 h and then treated with 1N aq. HCl until pH=2 was reached. Aqueous phase extracted with EtOAc and organic layer dried over Na2SO4 to get a white solid. MS (ES+) C26H30IN5O5 requires: 619. Found: 620 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionAqueous phase extracted with EtOAc and organic layer
  3. dry with materialdried over Na2SO4
  4. customto get a white solid

Sources & evidence

ORD record
ord-398397f34afb42618ffef7cddf58436d
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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