(2-Oxo-1,3-oxazolidin-3-yl)acetic acid → HCID 60152108, compound

HRID 85591Notes

Reaction equation

N[C@]12CC[C@@H](C(C)=C)[C@@H]1[C@@H]1[C@@](C)(CC2)[C@@]2(C)[C@@H]([C@]3(C)[C@@H](CC2)C(C)(C)C(C2C=CC(C(OC)=O)=CC=2)=CC3)CC1.CN(C)CC[C:45]([NH:47][C@:48]12[CH2:82][CH2:81][C@@H:80]([C:83]([CH3:85])=[CH2:84])[C@@H:49]1[C@@H:50]1[C@@:63]([CH3:66])([CH2:64][CH2:65]2)[C@@:62]2([CH3:67])[C@@H:53]([C@:54]3([CH3:79])[C@@H:59]([CH2:60][CH2:61]2)[C:58]([CH3:69])([CH3:68])[C:57]([C:70]2[CH:78]=[CH:77][C:73]([C:74]([OH:76])=[O:75])=[CH:72][CH:71]=2)=[CH:56][CH2:55]3)[CH2:52][CH2:51]1)=[O:46].[O:87]=[C:88]1[N:92]([CH2:93]C(O)=O)[CH2:91][CH2:90][O:89]1>>[CH3:66][C@:63]12[C@@:62]3([CH3:67])[C@@H:53]([C@:54]4([CH3:79])[C@@H:59]([CH2:60][CH2:61]3)[C:58]([CH3:69])([CH3:68])[C:57]([C:70]3[CH:78]=[CH:77][C:73]([C:74]([OH:76])=[O:75])=[CH:72][CH:71]=3)=[CH:56][CH2:55]4)[CH2:52][CH2:51][C@@H:50]1[C@H:49]1[C@H:80]([C:83]([CH3:85])=[CH2:84])[CH2:81][CH2:82][C@:48]1([NH:47][C:45](=[O:46])[CH2:93][N:92]1[CH2:91][CH2:90][O:89][C:88]1=[O:87])[CH2:65][CH2:64]2

Participants

Reactant 3

HCID 12676756(2-Oxo-1,3-oxazolidin-3-yl)acetic acid

HCID 683578604-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(dimethylamino)propanamido)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HCID 68357865methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Product 1

HCID 60152108HCID 60152108, compoundYield 29%

Procedure

The title compound was prepared in 29% yield from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate following the same procedure as described for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(dimethylamino)propanamido)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid, except 2-(2-oxooxazolidin-3-yl)acetic acid was used instead of 3-(dimethylamino)propionic acid hydrochloride in Step 1. LCMS: m/e 657.5 (M+H)+, 1.97 min (method 6). 1H NMR (500 MHz, 1:1 CDCl3:MeOD) δ=7.92 (d, J=8.2 Hz, 2H), 7.20 (d, J=8.5 Hz, 2H), 6.82 (s, 1H), 5.29 (dd, J=1.7, 6.3 Hz, 1H), 4.76 (d, J=1.5 Hz, 1H), 4.64 (s, 2H), 4.43 (dt, J=1.7, 8.2 Hz, 2H), 3.98-3.84 (m, 2H), 3.74 (t, J=8.1 Hz, 2H), 2.69-2.56 (m, 2H), 2.40 (dd, J=8.1, 12.4 Hz, 1H), 2.13 (dd, J=6.4, 17.1 Hz, 1H), 1.98-1.81 (m, 2H), 1.81-1.75 (m, 1H), 1.73 (br. s., 1H), 1.71 (s, 3H), 1.70-1.65 (m, 1H), 1.61-1.43 (m, 7H), 1.42-1.29 (m, 4H), 1.29-1.21 (m, 2H), 1.16-1.12 (m, 1H), 1.10 (s, 3H), 1.02 (s, 3H), 1.02 (s, 3H), 0.95 (s, 3H), 0.94 (s, 3H).

Workup

customm/e 657.5 (M+H)+, 1.97 min (method 6)

Sources & evidence

ORD record: ord-f53c164419bb473eb6ebe7638ee379ea
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

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