Triphenylphosphine → 4-[2-(2-Aminothiazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

HRID 1599914Notes

Reaction equation

HRID 1599914 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@@H:7]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH2:49][C:50]1[S:51][CH:52]=[C:53]([CH2:55][CH2:56]O)[N:54]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:29])[C@@H:7]([NH:19][S:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:56][CH2:55][C:53]2[N:54]=[C:50]([NH2:49])[S:51][CH:52]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 158507264-Hydroxybenzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl esterHCID 158507592-(2-Amino-1,3-thiazol-4-yl)ethan-1-ol

Product 1

HCID 158507274-[2-(2-Aminothiazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-2 (0.14 g, 0.32 mmol) and PPh3 (0.11g, 0.41 mmol) in THF (2 mL) at ambient temperature was added a solution of 5-4 (56 μg, 0.39 mmol) DEAD (67 μL, 0.42 mmol) in THF (2 mL) dropwise over a 15 min period. After 72 h, the reaction mixture was diluted with EtOAc and then washed with H2O, sat. NaHCO3, 10% KHSO4 and brine, dried (MgSO4) and concentrated. After two flash columns: silica, 85% EtOAc/hexanes; silica, 5% to 30% isopropanol/CHCl3), 5-5 was obtained as a yellow oil. Rf 0.19 (silica, 85% EtOAc/hexanes).

Workup

  1. washwashed with H2O, sat. NaHCO3, 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customsilica, 5% to 30% isopropanol/CHCl3), 5-5 was obtained as a yellow oil

Sources & evidence

ORD record
ord-cb71239b122145f19e5157ebe0afe3c5
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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