(R)-Solketal → (R)-tert-Butoxycarbonylamino-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid

HRID 561995Notes

Reaction equation

HRID 561995 reaction equation
IC1C=CC(C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=CC=1.C1(C[C@H]2NC(=O)N([C@H](C3NC(C4C=CC(I)=CC=4F)=C(C)N=3)[C@H](C3C=CC=CC=3)C)C2=O)CC1.N[C@H](C1C=CC(OC[C@@H](O)CO)=CC=1)C(N[C@H](C1NC(C2C=CC(I)=CC=2F)=C(Cl)N=1)[C@H](C1C=CC=CC=1)C)=O.[C:103]([O:107][C:108]([NH:110][C@H:111]([C:115]1[CH:120]=[CH:119][C:118]([O:121][CH2:122][C@H:123]2[CH2:127][O:126][C:125]([CH3:129])([CH3:128])[O:124]2)=[CH:117][CH:116]=1)[C:112]([OH:114])=[O:113])=[O:109])([CH3:106])([CH3:105])[CH3:104].CC1(C)O[C@H](CO)CO1>>[C:103]([O:107][C:108]([NH:110][C@H:111]([C:115]1[CH:120]=[CH:119][C:118]([O:121][CH2:122][C@@H:123]2[CH2:127][O:126][C:125]([CH3:129])([CH3:128])[O:124]2)=[CH:117][CH:116]=1)[C:112]([OH:114])=[O:113])=[O:109])([CH3:106])([CH3:104])[CH3:105]

Participants

6

Reactant 5

HCID 736056(R)-SolketalHCID 577719783-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acidHCID 178432851HCID 178432851, compoundHCID 178461665HCID 178461665, compound

Product 1

HCID 67001504(R)-tert-Butoxycarbonylamino-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid

Procedure

Prepared by the same method as described in example 1 except that (i) (R)-tert-butoxycarbonylamino-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 74-G and (ii) cyclization of (R)-2-amino-N-{(1S,2S)-1-[4-chloro-5-(2-fluoro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-acetamide in step 74-H was performed as described in step 34-H. (R)-tert-Butoxycarbonylamino-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid was prepared as described in steps 33-T and 33-U except that in step 70-T (R)-2,2-dimethyl-1,3-dioxolane-4-methanol was used in place of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol. HR-MS: calcd for C30H27ClFlN4O5 [M+H+] 705.0772. Found 705.0771.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-c994a3c8124144fe97b8d981979935ca
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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