Acetonitrile → HCID 53386421, compound

HRID 1898553Notes

Reaction equation

HRID 1898553 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([C:6]#[N:7])[CH2:2]1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.CC(O[C:18]([NH:20][C@@H:21]([C:25]([OH:27])=O)[CH:22]1[CH2:24][CH2:23]1)=[O:19])(C)C.C([NH:35][C@@H:36]([C:41](O)=O)[C:37]([CH3:40])([CH3:39])C)(OC(C)(C)C)=O.FC(F)(F)CO.[F-].[Cs+].C(#[N:54])C>>[C:6]([C@@H:3]1[CH2:4][CH2:5][N:1]([C:25](=[O:27])[C@H:21]([NH:20][C:18]([C:10]2[C:11]3[C:12](=[N:54][CH:41]=[C:36]([CH:37]4[CH2:39][CH2:40]4)[N:35]=3)[NH:8][CH:9]=2)=[O:19])[CH:22]2[CH2:23][CH2:24]2)[CH2:2]1)#[N:7]

Participants

8

Reactant 7

HCID 6342AcetonitrileHCID 64092,2,2-TrifluoroethanolHCID 25953Cesium fluorideHCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 34180556HCID 34180556, compound

Product 1

HCID 53386421HCID 53386421, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting (R)-pyrrolidine-3-carbonitrile for pyrrolidine and Boc-D-cyclopropyl glycine for Boc-D-tert-leucine. N-Boc deprotection in step 2 was achieved using 2,2,2-trifluoroethanol in a microwave reactor. SEM deprotection in step 4 was achieved using CsF in refluxing acetonitrile. MS: (M+H)+=379.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ff3d20c7ac444b47b9c7f58993ccf4a4
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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