{(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester → A 410099.1, amine-Boc

HRID 1481925Notes

Reaction equation

C(OC(=O)N([C@H](C(=O)N[C@@H](C1CCCCC1)C(N1C[C@@H](N)C[C@H]1C(=O)NCC1C=CC=CC=1)=O)C)C)(C)(C)C.C1C2C(COC(=O)[NH:56][C@H:57]3[CH2:61][C@@H:60]([C:62](=[O:74])[NH:63][C@H:64]4[C:73]5[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=5)[CH2:67][CH2:66][CH2:65]4)[N:59]([C:75](=[O:97])[C@@H:76]([NH:83][C:84](=[O:96])[C@@H:85]([N:87]([C:89]([O:91][C:92]([CH3:95])([CH3:94])[CH3:93])=[O:90])[CH3:88])[CH3:86])[CH:77]4[CH2:82][CH2:81][CH2:80][CH2:79][CH2:78]4)[CH2:58]3)C3C(=CC=CC=3)C=2C=CC=1>>[C:92]([O:91][C:89](=[O:90])[N:87]([C@H:85]([C:84](=[O:96])[NH:83][C@@H:76]([CH:77]1[CH2:78][CH2:79][CH2:80][CH2:81][CH2:82]1)[C:75]([N:59]1[CH2:58][C@@H:57]([NH2:56])[CH2:61][C@H:60]1[C:62](=[O:74])[NH:63][C@H:64]1[C:73]2[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=2)[CH2:67][CH2:66][CH2:65]1)=[O:97])[CH3:86])[CH3:88])([CH3:93])([CH3:94])[CH3:95]

Participants

Reactant 2

HCID 90220982{(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester2×

HCID 90231684{(S)-1-[(S)-2-((2S,4S)-4-Amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester2×

Product 1

HCID 90221030A 410099.1, amine-BocYield 99.5%

Procedure

In a similar manner to that described for {(S)-1-[(S)-2-((2S,4S)-4-amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (Intermediate 28, Step 2), {(3S,5S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (Intermediate 25) (500 mg, 0.62 mmol) was converted to the title compound (360 mg, foam).

Sources & evidence

ORD record: ord-483362735ee24c628fccd54c47d06fc4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409888B2

Reaction notes

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