Phenyl isocyanate → HCID 69018058, compound

HRID 541617Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[NH2:15][C@@H:16]([CH2:43][OH:44])[C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:24][C:25]3[N:41]=[C:29]([NH:30][C:31]4[CH:32]=[CH:33][CH:34]=[C:35]([CH:40]=4)[CH2:36][CH2:37][C:38]=1[CH:39]=2)[N:28]=[CH:27][C:26]=3[Cl:42])=[O:18].[C:45]1([N:51]=[C:52]=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:51]([C:52]([NH:15][C@@H:16]([CH2:43][OH:44])[C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:24][C:25]3[N:41]=[C:29]([NH:30][C:31]4[CH:32]=[CH:33][CH:34]=[C:35]([CH:40]=4)[CH2:36][CH2:37][C:38]=1[CH:39]=2)[N:28]=[CH:27][C:26]=3[Cl:42])=[O:18])=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 86636145HCID 86636145, compound

Product 1

HCID 69018058HCID 69018058, compoundYield 36%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using (2S)-2-amino-N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-3-hydroxypropanamide bis(trifluoroacetate) and phenyl isocyanate as starting materials in 36% yield. LCMS for C28H27ClN7O3 (M+H)+: m/z=544.2.

Sources & evidence

ORD record: ord-d04a11e487074975be1397d71d25281d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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