Hydrochloric Acid → HCID 136387747, compound

HRID 1924387Notes

Reaction equation

HRID 1924387 reaction equation
[CH2:1]([C:3]1[C:4]2[C:27]3=[CH:28][C: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:6][CH:5]=2)[CH3:2].[Li+].[OH-].Cl>C1COCC1.O>[CH2:1]([C:3]1[C:4]2[C:27]3=[CH:28][C: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]([OH:32])=[O:31])=[N:14][N:13]=4)=[CH:6][CH:5]=2)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 136387746HCID 136387746, compound

Product 1

HCID 136387747HCID 136387747, compound

Reagents, catalysts & solvents 1

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

Procedure

To a solution of methyl (3R,5S,8S)-22-ethyl-8-isopropyl-7-oxo-2,27-dioxa-6,9,11,12,24-pentaazapentacyclo[16.6.2.13,6.110,13.021,25]octacosa-1(24),10,12,18,20,22,25-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. The aqueous phase was extracted with EtOAc, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a white solid. MS (ES+) C27H33N5O5 requires: 507. Found: 508 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aqueous phase was extracted with EtOAc
  3. customthe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white solid

Sources & evidence

ORD record
ord-9bd004dd72664716862d63167c326dbf
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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