Trimethylphosphine → Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2172995Notes

Reaction equation

HRID 2172995 reaction equation
CP(C)C.[N:5]([C@H:8]1[C@@H:13]2[C@@H:11]([C@H:12]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@:10]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:9]1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1)=[N+]=[N-].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[NH2:5][C@H:8]1[C@@H:13]2[C@@H:11]([C@H:12]2[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@:10]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@@H:9]1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1

Participants

6

Reactant 3

HCID 68983TrimethylphosphineHCID 516892Sodium BicarbonateHCID 86695978Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-azido-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Product 1

HCID 86695979Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add a 1M solution of trimethylphosphine in tetrahydrofuran (19.56 mL, 19.56 mmol) to di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-azido-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (8.00 g, 13.04 mmol) in tetrahydrofuran (43.46 mL) and water (130.39 mL) at room temperature and stir overnight. Saturated aqueous sodium bicarbonate is added to the reaction then extracted with ethyl acetate (3×). The combined organics are washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving the title compound (7.42 g, 12.63 mmol, 97%). MS (m/z): 609/611 (M+Na).

Workup

  1. extractionthen extracted with ethyl acetate (3×)
  2. washThe combined organics are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6eb075e923424ea28dd2f086c6780517
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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