Tributylphosphine → HCID 18536158, compound

HRID 412172Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[NH:16][C:17](=O)[CH2:18][NH:19][CH2:20][CH2:21][C:22]2[N:23](CCO)[CH2:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(P(CCCC)CCCC)CCC.[CH3:63][C:64]([O:67]C(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1>[CH3:1][S:2]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[N:16]2[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][C:22]3[N:23]=[CH:24][N:25]([C:27]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:26]=3)[CH2:63][C:64]2=[O:67])=[CH:8][CH:7]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product from Step F (60.5 mmol) in 500 mL of tetrahydrofuran was added tributylphosphine (25 mL, 100 mmol). After cooling to 0° C., di-tert-butylazodicarboxylate (23 g, 100 mmol) was added, and the reaction was allowed to come to room temperature for 2 hours. The solution was concentrated in vacuo, partitioned between EtOAc and water, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide the titled product (45.0 g). The crude product was purified by silica gel chromatography (5% MeOH/CHCl3) to provide the pure titled product along with impure fractions.

Workup

concentrationThe solution was concentrated in vacuo
custompartitioned between EtOAc and water
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-06a3273245854387bd464a61a982f913
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562823B1

Reaction notes

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