HCID 87385266, compound → HCID 87390692, compound

HRID 2204962Notes

Reaction equation

HRID 2204962 reaction equation
[C:1]([O:14][C@H:15]([CH2:61][O:62][C:63](=[O:75])[CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74])[CH2:16][S:17][CH2:18][C@H:19]([NH:43][C:44]([O:46][CH2:47][CH:48]1[C:60]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45])[C:20](=[O:42])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[C:63]([O:62][CH2:61][C@@H:15]([O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:16][S:17][CH2:18][C@H:19]([NH:43][C:44]([O:46][CH2:47][CH:48]1[C:60]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45])[C:20](=[O:42])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH2:34])(=[O:75])[CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74]

Participants

4

Reactant 1

HCID 87385266HCID 87385266, compound

Product 1

HCID 87390692HCID 87390692, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(20R,24R)-20-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2,2-dimethyl-4,19-dioxo-3,9,14-trioxa-22-thia-5,18-diazapentacosane-24,25-diyl didodecanoate was stirred in 30% TFA/DCM for 4 hours at room temperature. The reaction was then diluted with DCM and washed with 1M citric acid (pH3). The organics were then dried over anhydrous Na2SO4, filtered and concentrated to afford (2R,6R)-6-(((9H-fluoren-9-yl)methoxy)carbonylamino)-20-amino-7-oxo-12,17-dioxa-4-thia-8-azaicosane-1,2-diyl didodecanoate.

Workup

  1. washwashed with 1M citric acid (pH3)
  2. dry with materialThe organics were then dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-57eb8ccecd2841d1b2b121859f01e231
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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