Triphenylphosphine → HCID 66877137, compound

HRID 1863977Notes

Reaction equation

HRID 1863977 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]([N:30]1[CH2:35][C@H:34]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]3[O:46][CH2:45][CH2:44][N:43]([CH2:47][CH2:48][CH2:49][O:50][CH3:51])[C:42]=3[CH:52]=2)[C@@H:33]([C:53]2[CH:58]=[CH:57][C:56]([CH2:59][O:60][CH2:61][C@@H:62]([CH3:66])[CH2:63][O:64][CH3:65])=[CH:55][CH:54]=2)[C@H:32]([CH2:67][N:68]=[N+]=[N-])[CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.O1CCCC1.O.N>[CH2:20]([O:27][C:28]([N:30]1[CH2:35][C@H:34]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]3[O:46][CH2:45][CH2:44][N:43]([CH2:47][CH2:48][CH2:49][O:50][CH3:51])[C:42]=3[CH:52]=2)[C@@H:33]([C:53]2[CH:58]=[CH:57][C:56]([CH2:59][O:60][CH2:61][C@@H:62]([CH3:66])[CH2:63][O:64][CH3:65])=[CH:55][CH:54]=2)[C@H:32]([CH2:67][NH2:68])[CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 2

HCID 11776TriphenylphosphineHCID 86629099HCID 86629099, compound

Product 1

HCID 66877137HCID 66877137, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.128 mmol of triphenylphosphine are added to a solution of 5.940 mmol of (3S,4R,5R)-3-azidomethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester in 20 ml of methanol, 20 ml of tetrahydrofuran, 5 ml of water and 3.56 ml of concentrated aqueous ammonia (25%) at room temperature. After overnight stirring, the reaction mixture is partitioned between tert-butyl methyl ether and 5:1 water/saturated aqueous sodium bicarbonate solution. The aqueous layer is extracted with tert-butyl methyl ether—the combined organic layers are washed successively with water and brine, dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound as a yellow oil. Rf=0.42 (dichloromethane-methanol-25% ammonia conc. 200:20:1); Rt=4.64 (gradient I).

Workup

  1. customthe reaction mixture is partitioned between tert-butyl methyl ether and 5:1 water/saturated aqueous sodium bicarbonate solution
  2. extractionThe aqueous layer is extracted with tert-butyl methyl ether—the combined organic layers
  3. washare washed successively with water and brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customThe residue is purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-949a414a1d9549018559b49ecdf62e7a
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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