Acetonitrile → HCID 58438597, compound

HRID 1898555Notes

Reaction equation

HRID 1898555 reaction equation
C(O)(=O)C(O)=O.[CH2:7]1[C:10]2([CH2:13][NH:12][CH2:11]2)[CH2:9][O:8]1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CC(O[C:24]([NH:26][C@@H:27]([C:31]([OH:33])=O)[CH:28]1[CH2:30][CH2:29]1)=[O:25])(C)C.C([NH:41][C@@H:42]([C:47](O)=O)[C:43]([CH3:46])([CH3:45])C)(OC(C)(C)C)=O.FC(F)(F)CO.[F-].[Cs+].C(#[N:60])C>>[CH:28]1([C@@H:27]([NH:26][C:24]([C:16]2[C:17]3[C:18](=[N:60][CH:47]=[C:42]([CH:43]4[CH2:45][CH2:46]4)[N:41]=3)[NH:14][CH:15]=2)=[O:25])[C:31]([N:12]2[CH2:13][C:10]3([CH2:9][O:8][CH2:7]3)[CH2:11]2)=[O:33])[CH2:29][CH2:30]1

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 53308464Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)

Product 1

HCID 58438597HCID 58438597, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 2-oxa-6-aza-spiro[3.3]heptane oxalate 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)+=382.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-36409e6b2ca746f2ae152b119a728ddc
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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