Triphenylphosphine → HCID 13036853, compound

HRID 1156740Notes

Reaction equation

HRID 1156740 reaction equation
N#N.[C:3]1([CH2:9][O:10][C:11]([NH:13][C@H:14]([C:17]([NH:19][O:20]CC(NC(OCC2C=CC=CC=2)=O)C(OC)=O)=[O:18])[CH2:15]O)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.CCCCCCC=CCCC>O1CCCC1>[OH:20][N:19]1[CH2:15][C@H:14]([NH:13][C:11]([O:10][CH2:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:12])[C:17]1=[O:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 136496Undec-4-eneHCID 5462977Diethyl azodicarboxylateHCID 86738442HCID 86738442, compound

Product 1

HCID 13036853HCID 13036853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0°-5° C.) solution of N2 -[[(phenylmethyl)oxy]carbonyl]-N-[2-[[[(phenylmethyl)oxy]carbonyl]amino]-3-methoxy-3-oxopropoxy]-L-serinamide (6.08 g) in distilled tetrahydrofuran (100 ml) is added triphenylphosphine (3.6 g) followed by diethylazodicarboxylate (2.15 ml, 2.38 g). The reaction mixture is allowed to stir for twelve hours under nitrogen, whereupon 7.0 ml of 1,8-diazabicyclo[5.4.0.]undecan-7-ene is added. After 30 minutes, tetrahydrofuran is removed by evaporation and the resulting residue is partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer is washed once with ethyl acetate, then adjusted to pH 2 with saturated potassium bisulfate, and extracted with ethyl acetate (five times). The combined extracts are dried and concentrated to a crystalline solid (1.8 g). A portion is recrystallized from acetone/hexane (two times) to give an analytical sample, melting point 128°-131° C.

Workup

  1. customtetrahydrofuran is removed by evaporation
  2. customthe resulting residue is partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe aqueous layer is washed once with ethyl acetate
  4. extractionextracted with ethyl acetate (five times)
  5. customThe combined extracts are dried
  6. concentrationconcentrated to a crystalline solid (1.8 g)
  7. customA portion is recrystallized from acetone/hexane (two times)
  8. customto give an analytical sample, melting point 128°-131° C.

Sources & evidence

ORD record
ord-4998b85573f74825b01a52401de96e4f
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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