HCID 18992094, compound → HCID 88404105, compound

HRID 375720Notes

Reaction equation

C(OC1C(CBr)=C(C(C)=C(OC(=O)C)C=1)C(OCC(Cl)(Cl)Cl)=O)(=O)C.OC[C@H](NC(=O)OC(C)(C)C)C(=O)NCCS.[C:43]([O:46][C:47]1[C:48]([CH3:83])=[C:49]([C:58]([CH2:65][S:66][C@@H:67]([NH:69][C:70](=[O:82])[C@@H:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:72][OH:73])[CH3:68])=[C:59]([O:61][C:62](=[O:64])[CH3:63])[CH:60]=1)[C:50]([O:52]CC(Cl)(Cl)Cl)=[O:51])(=[O:45])[CH3:44]>>[C:43]([O:46][C:47]1[C:48]([CH3:83])=[C:49]([C:58]([CH2:65][S:66][CH:67]([NH:69][C:70](=[O:82])[C@@H:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:72][OH:73])[CH3:68])=[C:59]([O:61][C:62](=[O:64])[CH3:63])[CH:60]=1)[C:50]([OH:52])=[O:51])(=[O:45])[CH3:44]

Participants

Reactant 3

HCID 18992094HCID 18992094, compound

HCID 53694135HCID 53694135, compound

HCID 88403770HCID 88403770, compound

Product 1

HCID 88404105HCID 88404105, compound

Procedure

2,2,2-Trichloroethyl 3,5-diacetoxy-2-bromomethyl-6-methylbenzoate was reacted with t-butyl [(S)-2-hydroxy-1-[(2-mercaptoethyl)carbamoyl]ethyl]carbamate in a manner analogous to the procedure given in Example 1(f), and the resulting 2,2,2-trichloroethyl 3,5-diacetoxy-6-[[((R)-2-[(S)-2-(t-butoxyformamido)-3-hydroxypropionamido]-2-ethyl]thio]methyl]-2-methylbenzoate product was subjected in analogous manner to the procedure described in Example 1(g) to give 3,5-diacetoxy-6-[[[2-[(S)-2-(1-t-butoxyformamido)-3-hydroxypropionamido]-2-ethyl]thio]methyl]-2-methylbenzoic acid as an oil.

Sources & evidence

ORD record: ord-61a5fc68460645aab83102855aa60924
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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