{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester trifluoroacetate → ((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid methyl ester

HRID 2382421Notes

Reaction equation

FC(F)(F)[C:3]([OH:5])=O.C(O[C:13](=[O:56])[NH:14][C@@H:15]1[CH2:19][CH2:18][N:17]([C:20]2[N:28]=[C:27]3[C:23]([N:24]=[CH:25][N:26]3[C@@H:29]3[CH2:33][C@H:32]([NH:34][C:35](=[O:38])CC)[C@@H:31]([OH:39])[C@H:30]3[OH:40])=[C:22]([NH:41][CH2:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:21]=2)[CH2:16]1)(C)(C)C.ClC1N=C2C(N=C[N:64]2[C@@H:67]2[CH2:71][C@H:70]([NH:72]C(=O)CC)[C@@H:69](O)[C@H]2O)=C(NCC(C2C=CC=CC=2)C2C=CC=CC=2)N=1.COC(=O)N[C@H]1C[C@@H](N2C=NC3C2=NC(Cl)=NC=3NCC(C2C=CC=CC=2)C2C=CC=CC=2)[C@H](O)[C@@H]1O>>[CH3:3][O:5][C:35](=[O:38])[NH:34][C@H:32]1[CH2:33][C@@H:29]([N:26]2[CH:25]=[N:24][C:23]3[C:27]2=[N:28][C:20]([N:17]2[CH2:18][CH2:19][C@@H:15]([NH:14][C:13]([NH:72][C@@H:70]4[CH2:71][CH2:67][NH:64][CH2:69]4)=[O:56])[CH2:16]2)=[N:21][C:22]=3[NH:41][CH2:42][CH:43]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C@H:30]([OH:40])[C@@H:31]1[OH:39]

Participants

Reactant 3

HCID 66630463{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester trifluoroacetate

HCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

HCID 86632436{(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid methyl ester2×

Product 1

HCID 66630720((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid methyl ester

Procedure

This compound is prepared analogously to {(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester trifluoroacetate (Example 18 step 1) by replacing N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Intermediate J) with {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-carbamic acid methyl ester (Intermediate T) and by replacing (3R)-(+)-(3-Boc-amino)pyrrolidine with 1,3-di(R)-pyrrolidin-3-yl-urea (Intermediate B). (MH+ 685.2)

Sources & evidence

ORD record: ord-083272a243ee4fdca7d3c331ea77196f
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258141B2

Reaction notes

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