Triphenylphosphine → (3s,5s)-Thioacetic acid s-[5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl] ester

HRID 1006841Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:34]([O:41][CH2:42][C@H:43]1[N:47]([S:48]([C:51]2[CH:60]=[CH:59][C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH:52]=2)(=[O:50])=[O:49])[CH2:46][C@H:45](O)[CH2:44]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:62]([OH:65])(=[S:64])[CH3:63]>O1CCCC1>[CH2:34]([O:41][CH2:42][C@H:43]1[N:47]([S:48]([C:51]2[CH:60]=[CH:59][C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH:52]=2)(=[O:49])=[O:50])[CH2:46][C@@H:45]([S:64][C:62](=[O:65])[CH3:63])[CH2:44]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of triphenylphosphine (2.92 g) in tetrahydrofuran (30 ml) was added diisopropylazodicarboxylate (2.20 ml) within 5 minutes at 0° C. The solution was stirred for 0.5 h at 0° C., then a solution of (3R,5S)-5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-ol (2.2 g) and thioacetic acid (0.81 ml) in tetrahydrofurane (10 ml) were added to the suspension within 0.5 h at 0° C. Stirring was continued for 1 h at 0° C. and 1 h at room temperature. The reaction mixture was concentrated, and the residue was chromatographed on silica gel using EtOAc/hexane 1:4 and 1:3 as eluents to obtain (3S,5S)-thioacetic acid S-[5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl] ester (2.1 g) as a syrup, MS: 456 (MH+).

Workup

stirringStirring
waitwas continued for 1 h at 0° C. and 1 h at room temperature
concentrationThe reaction mixture was concentrated
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-b9a8d9313ed641e4849d9d5878866851
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

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