Acetonitrile → HCID 58438617, compound

HRID 1898557Notes

Reaction equation

HRID 1898557 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.CC(O[C:19]([NH:21][C@@H:22]([C:26]([OH:28])=O)[CH:23]1[CH2:25][CH2:24]1)=[O:20])(C)C.C([NH:36][C@@H:37]([C:42](O)=O)[C:38]([CH3:41])([CH3:40])C)(OC(C)(C)C)=O.FC(F)(F)CO.[F-].[Cs+].C(#[N:55])C>>[CH:23]1([C@@H:22]([NH:21][C:19]([C:11]2[C:12]3[C:13](=[N:55][CH:42]=[C:37]([CH:38]4[CH2:40][CH2:41]4)[N:36]=3)[NH:9][CH:10]=2)=[O:20])[C:26]([N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)=[O:28])[CH2:24][CH2:25]1

Participants

8

Reactant 7

HCID 6342AcetonitrileHCID 64092,2,2-TrifluoroethanolHCID 25953Cesium fluorideHCID 31268PyrrolidineHCID 6484228Thiomorpholine 1,1-dioxideHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid

Product 1

HCID 58438617HCID 58438617, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting thiomorpholine-1,1-dioxide 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)+=418.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4b606fa44e4f41fcb1d13f21f4e0864e
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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