Ammonia → tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

HRID 500015Notes

Reaction equation

HRID 500015 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C@@H:13]([OH:29])[CH2:14][C@H:15]([C:19](=[O:28])[NH:20][CH2:21][C:22]([C:25](=[O:27])[NH2:26])([CH3:24])[CH3:23])[CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10]([CH:30]([CH3:32])[CH3:31])[C@@H:9]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N.[Li].[Cl-].[NH4+]>O1CCCC1.C(O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:12]([CH2:11][C@H:10]([CH2:9][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=1)[CH:30]([CH3:32])[CH3:31])[C@@H:13]([OH:29])[CH2:14][C@H:15]([C:19](=[O:28])[NH:20][CH2:21][C:22]([C:25](=[O:27])[NH2:26])([CH3:23])[CH3:24])[CH:16]([CH3:17])[CH3:18])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 11998976HCID 11998976, compound

Product 1

HCID 53348234tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 0.037 g of amide 12 is dissolved in 1 mL of tetrahydrofurane and cooled to −78° C. Liquid ammonia is added followed by 0.0042 g of lithium metal. The deep blue solution is stirred for 2 hours at −78° C., and then 0.35 g of ethanol is added and the mixture is stirred for 30 minutes at −78° C. Ammonium chloride (0.15 g) is added and the mixture is warmed to room temperature. The organic phase is partitioned between water and ethyl acetate. The organic phase is separated and the solvent removed in vacuum. The residue is stirred with heptane and filtered. Removal of the heptane produces 13 identical with an authentic sample. M++H=652

Workup

  1. stirringthe mixture is stirred for 30 minutes at −78° C
  2. temperaturethe mixture is warmed to room temperature
  3. customThe organic phase is partitioned between water and ethyl acetate
  4. customThe organic phase is separated
  5. customthe solvent removed in vacuum
  6. stirringThe residue is stirred with heptane
  7. filtrationfiltered
  8. customRemoval of the heptane

Sources & evidence

ORD record
ord-b182b95923df444ab9c555312d15ff6e
Source dataset
uspto-grants-2010_08
Patent number
US07767831B2

Reaction notes

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