1,2-Dichloroethane → HCID 86612273, compound

HRID 1441976Notes

Reaction equation

HRID 1441976 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH2:22][C@H:23]([N:28]([C:30](=[O:54])[C@H:31]([NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[CH:16]=2)=[CH:11][C:10]=1[CH2:55][C@H:56]([NH:60][C:61]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])[C:57]([OH:59])=[O:58])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:71][C:72]1[C:77](O)=[C:76]([F:79])[C:75]([F:80])=[C:74]([F:81])[C:73]=1[F:82].C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH2:22][C@H:23]([N:28]([C:30](=[O:54])[C@H:31]([NH:46][C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[O:37])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[CH:16]=2)=[CH:11][C:10]=1[CH2:55][C@H:56]([NH:60][C:61]([O:63][CH2:64][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)=[O:62])[C:57]([O:59][C:77]1[C:76]([F:79])=[C:75]([F:80])[C:74]([F:81])=[C:73]([F:82])[C:72]=1[F:71])=[O:58])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 86612274HCID 86612274, compound

Product 1

HCID 86612273HCID 86612273, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.89 g (crude product, about 0.922 mmol) of (2S)-3-(4-(benzyloxy)-3′-{(2S)-2-[{(2R)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}(methyl)amino]-3-methoxy-3-oxopropyl}-4′-fluorobiphenyl-3-yl)-2-{[(benzyloxy)carbonyl]amino}-propionic acid (Example 20O) are introduced into 50 ml of dichloromethane. At −25° C., 0.85 g (4.61 mmol) of pentafluorophenol, 0.21 g (1.11 mmol) of EDC and 45 mg (0.37 mmol) of DMAP are added under argon. The mixture slowly warms to RT overnight. The reaction mixture is concentrated in vacuo and briefly dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custombriefly dried under high vacuum
  3. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-b91c2e8d858e4a208422ec5d80f42867
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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